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| Dec 1, 2008 |
| Allen County-Scottsville |
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vs. Caverna |
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| Community Christian (Paducah) |
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vs. Fulton County |
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| Fulton City |
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vs. Mayfield |
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| June Buchanan |
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vs. Jenkins |
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| Livingston Central |
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vs. St. Mary |
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| Paducah Tilghman |
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vs. Hickman County |
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| Phelps |
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vs. Hurley, VA |
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| Pickett County, TN |
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vs. Clinton County |
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| South Floyd |
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vs. Riverside Christian |
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| Southern |
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vs. Valley |
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| Todd County Central |
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vs. Fort Campbell |
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| Walton-Verona |
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vs. Cooper |
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| Dec 2, 2008 |
| Apollo |
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vs. Warren Central |
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| Atherton |
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vs. Jeffersontown |
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| Ballard Memorial |
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vs. Murray |
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| Bell County |
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vs. Claiborne, TN |
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| Berea |
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vs. Lynn Camp |
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| Boone County |
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vs. Ryle |
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| Bourbon County |
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vs. Bracken County |
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| Breathitt County |
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vs. June Buchanan |
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| Breckinridge County |
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vs. Grayson County |
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| Bullitt East |
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vs. Whitefield Academy |
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| Burgin |
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vs. Portland Christian |
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| Butler |
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vs. Central |
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| Calvary Christian |
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vs. Heritage Academy |
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| Carlisle County |
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vs. Livingston Central |
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| Casey County |
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vs. Anderson County |
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| Central Hardin |
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vs. Muhlenberg North |
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| Conner |
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vs. Dixie Heights |
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| Cordia |
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vs. South Floyd |
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| Dawson Springs |
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vs. McLean County |
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| Deming |
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vs. Augusta |
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| Doss |
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vs. Male |
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| DuPont Manual |
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vs. North Hardin |
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| East Jessamine |
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vs. Boyle County |
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| Eastern |
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vs. St. Xavier |
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| Elizabethtown |
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vs. Adair County |
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| Fern Creek |
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vs. Brown |
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| Fort Campbell |
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vs. Webster County |
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| Frederick Fraize |
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vs. Fort Knox |
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| Fulton County |
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vs. Heath |
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| George Rogers Clark |
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vs. North Laurel |
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| Glasgow |
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vs. Frankfort |
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| Grant County |
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vs. Harrison County |
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| Graves County |
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vs. Caruthersville, MO |
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| Green County |
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vs. Campbellsville |
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| Greenwood |
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vs. Allen County-Scottsville |
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| Hazard |
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vs. Estill County |
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| Hickman County |
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vs. Lone Oak |
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| Jackson County |
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vs. Owsley County |
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| Jenkins |
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vs. Knott County Central |
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| Kentucky Country Day |
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vs. St. Francis |
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| Kentucky School f/t Deaf |
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vs. Eminence |
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| Knox Central |
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vs. Harlan |
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| Lee County |
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vs. Buckhorn |
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| Lewis County |
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vs. Ashland Blazer |
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| Lloyd Memorial |
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vs. Spencer County |
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| Madison Southern |
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vs. Madison Central |
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| Madisonville-North Hopkins |
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vs. Ohio County |
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| Magoffin County |
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vs. Betsy Layne |
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| Marshall County |
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vs. Ullin Century, IL |
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| Mason County |
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vs. Highlands |
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| McCreary Central |
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vs. Mercer County |
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| Metcalfe County |
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vs. Warren East |
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| Model |
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vs. Bath County |
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| Montgomery County |
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vs. Lafayette |
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| Monticello |
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vs. Whitley County |
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| Muhlenberg South |
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vs. Edmonson County |
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| North Hardin Christian |
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vs. Evangel Christian |
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| Owen County |
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vs. Western Hills |
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| Paul Dunbar |
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vs. Tates Creek |
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| Pendleton County |
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vs. Campbell County |
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| Perry County Central |
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vs. Paintsville |
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| Pike County Central |
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vs. Allen Central |
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| Pineville |
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vs. Williamsburg |
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| Portland Christian |
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vs. Pleasure Ridge Park |
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| Powell County |
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vs. Jackson City |
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| Raceland |
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vs. West Carter |
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| Rowan County |
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vs. Fleming County |
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| Russell County |
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vs. Lincoln County |
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| Russellville |
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vs. Trinity (Whitesville) |
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| Sayre |
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vs. Menifee County |
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| Scott |
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vs. Silver Grove |
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| Shawnee |
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vs. Moore |
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| South Oldham |
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vs. Ludlow |
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| St. Henry |
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vs. St. Patrick |
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| TBA |
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vs. Hancock County |
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| Trimble County |
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vs. Henry County |
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| Union County |
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vs. Evansville Central, IN |
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| Valley |
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vs. Waggener |
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| Washington County |
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vs. Taylor County |
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| Wayne County |
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vs. Southwestern |
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| West Jessamine |
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vs. Rockcastle County |
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| Whitefield Academy |
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vs. Louisville Collegiate |
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| Williamstown |
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vs. Carroll County |
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| Dec 3, 2008 |
| Ervinton, VA |
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vs. Jenkins |
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| Fairdale |
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vs. Southern |
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| Newport |
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vs. Villa Madonna |
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| Oldham County |
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vs. Ryle |
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| Dec 4, 2008 |
| Ballard Memorial |
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vs. Dawson Springs |
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| Bath County |
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vs. Owsley County |
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| Berea |
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vs. Garrard County |
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| Bracken County |
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vs. St. Patrick |
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| Carroll County |
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vs. Trimble County |
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| Clinton County |
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vs. Monticello |
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| Cooper |
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vs. Holy Cross (Covington) |
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| Greenwood |
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vs. Butler County |
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| Harrisburg, IL |
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Calloway County
at Marshall County |
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| Hazard |
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vs. Buckhorn |
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| Hickman County |
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vs. Reidland |
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| Johnson Central |
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vs. Sheldon Clark |
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| Massac County, IL |
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Graves County
at Marshall County |
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| North Oldham |
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vs. Kentucky Country Day |
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| Paintsville |
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vs. Lawrence County |
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| Pineville |
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vs. Harlan County |
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| Powell County |
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vs. Wolfe County |
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| Russell County |
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vs. Casey County |
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| Silver Grove |
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vs. Bishop Brossart |
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| St. Henry |
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vs. Lexington Catholic |
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| Valley |
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vs. Whitefield Academy |
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| Webster County |
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vs. Hopkins County Central |
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| Western Hills |
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vs. Spencer County |
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| Dec 5, 2008 |
| Adair County |
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vs. Green County |
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| Allen County-Scottsville |
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vs. Franklin-Simpson |
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| Barbourville |
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vs. Middlesboro |
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| Bell County |
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vs. Leslie County |
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| Beth Haven |
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vs. Western |
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| Bethlehem |
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vs. John Hardin |
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| Boone County |
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vs. Walton-Verona |
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| Bourbon County |
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vs. Deming |
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| Bullitt East |
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vs. Bullitt Central |
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| Burgin |
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vs. J Frank White Academy, TN |
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| Casey County |
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vs. East Jessamine |
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| Christian County |
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vs. Warren Central |
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| Clay County |
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vs. Lexington Christian |
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| Cornerstone Christian |
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vs. North Hardin Christian |
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| Dayton |
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vs. Bracken County |
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| Dixie Heights |
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vs. Simon Kenton |
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| Doss |
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vs. Butler |
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| Elizabethtown |
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vs. Taylor County |
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| Elliott County |
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vs. Morgan County |
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| Estill County |
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vs. Perry County Central |
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| Fairview |
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vs. Green, OH |
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| Fleming County |
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vs. Ashland Blazer |
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| Fort Campbell |
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vs. Hopkinsville |
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| Frankfort |
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vs. Woodford County |
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| Frederick Fraize |
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vs. Breckinridge County |
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| Garrard County |
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vs. Southwestern |
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| Grayson County |
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vs. Muhlenberg South |
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| Greenup County |
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vs. Russell |
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| Hancock County |
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vs. Apollo |
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| Heath |
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vs. Ballard Memorial |
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| Henry County |
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vs. North Bullitt |
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| Jeffersontown |
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vs. Christian Academy-Louisville |
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| Johnson Central |
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vs. South Floyd |
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| Knott County Central |
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vs. South Floyd |
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| Knox Central |
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Paul Dunbar
at Clay County |
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| Letcher County Central |
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vs. East Ridge |
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| Lewis County |
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vs. Scott |
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| Ludlow |
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vs. Grant County |
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| Lynn Camp |
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vs. Williamsburg |
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| Madison Southern |
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vs. Washington County |
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| Marshall County |
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vs. Obion County Central, TN |
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| McCreary Central |
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vs. Pulaski County |
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| Mercer County |
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vs. Wayne County |
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| Metcalfe County |
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vs. Monroe County |
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| Model |
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vs. Eminence |
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| Moore |
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vs. Atherton |
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| Murray |
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vs. Lone Oak |
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| North Hardin |
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vs. Fort Knox |
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| North Laurel |
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vs. Lafayette |
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| Ohio County |
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vs. Barren County |
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| Paris |
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vs. Sayre |
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| Pendleton County |
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vs. Augusta |
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| Portland Christian |
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vs. Brown |
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| Prestonsburg |
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vs. Pikeville |
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| Riverside Christian |
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vs. Jackson City |
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| Rockcastle County |
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vs. Lincoln County |
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| Rowan County |
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vs. Raceland |
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| Russellville |
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vs. Logan County |
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| Ryle |
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vs. George Rogers Clark |
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| Shelby County |
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vs. Daviess County |
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| Somerset |
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vs. Boyle County |
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| St. Mary |
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vs. Community Christian (Paducah) |
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| St. Xavier |
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vs. Fern Creek |
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| TBA |
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Bryan Station
at Tates Creek |
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| Tennessee School for the Deaf |
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vs. Kentucky School f/t Deaf |
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| Trigg County |
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vs. Livingston Central |
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| Trinity (Louisville) |
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vs. Seneca |
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| Trinity (Whitesville) |
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vs. Evansville Day School, IN |
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| Valley |
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vs. St. Francis |
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| Villa Madonna |
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vs. Lloyd Memorial |
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| West Carter |
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vs. Boyd County |
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| Whitley County |
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vs. Corbin |
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| Dec 6, 2008 |
| Atlanta Area School for the Deaf |
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vs. Kentucky School f/t Deaf |
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| Barren County |
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vs. Warren East |
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| Bath County |
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vs. Rose Hill Christian |
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| Beth Haven |
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Frederick Fraize
at Hancock County |
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| Betsy Layne |
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vs. East Ridge |
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| Bowling Green |
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vs. Todd County Central |
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| Butler County |
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vs. Grayson County |
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| Calloway County |
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vs. University School, TN |
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| Campbellsville |
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vs. Glasgow |
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| Carlisle County |
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vs. Community Christian (Paducah) |
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| Daviess County |
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Meade County
at Hancock County |
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| DuPont Manual |
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vs. Atherton |
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| Edmonson County |
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Breckinridge County
at Hancock County |
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| Eminence |
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vs. Heritage Academy |
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| Fort Knox |
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vs. Cumberland County |
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| Frankfort |
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vs. Berea |
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| Graves County |
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vs. St. Mary |
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| Greenup County |
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vs. Elliott County |
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| Hancock County |
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vs. Logan County |
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| Harlan County |
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vs. Gate City, VA |
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| Henry County |
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vs. Model |
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| Hopkins County Central |
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vs. TBA |
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| Ironton, OH |
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vs. Ashland Blazer |
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| John Hardin |
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vs. Bullitt East |
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| Lake County, TN |
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vs. Fulton County |
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| Lexington Catholic |
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Paducah Tilghman
at Marshall County |
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| Lincoln County |
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vs. West Jessamine |
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| Madison Central |
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vs. Montgomery County |
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| Madisonville-North Hopkins |
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TBA
at Marshall County |
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| Marion County |
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vs. Waggener |
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| McLean County |
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vs. Crittenden County |
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| Muhlenberg North |
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Webster County
at Hopkins County Central |
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| Muhlenberg South |
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vs. Owensboro |
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| Nelson County |
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Southern
at |
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| Newport Central Catholic |
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vs. Holy Cross (Covington) |
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| Nicholas County |
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vs. Menifee County |
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| North Bullitt |
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vs. Washington County |
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| North Oldham |
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vs. Shawnee |
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| Ohio County |
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vs. Owensboro Catholic |
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| Paris |
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vs. St. Francis |
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| Pendleton County |
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vs. George Rogers Clark |
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| Phelps |
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vs. Pike County Central |
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| Pleasure Ridge Park |
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Elizabethtown
at |
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| Reidland |
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Dawson Springs
at Hopkins County Central |
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| Riverside Christian |
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vs. Burgin |
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| Russell |
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vs. Newport |
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| Shelby County |
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vs. Trinity (Louisville) |
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| Shelby Valley |
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vs. Paul Dunbar |
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| Silver Grove |
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vs. St. Patrick |
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| South Oldham |
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vs. Western Hills |
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| Spencer County |
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vs. Christian Academy-Louisville |
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| TBA |
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Harrison County
at Campbellsville |
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| TBA |
- |
vs. Christian County |
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| Trigg County |
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vs. Union County |
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| Trimble County |
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vs. Gallatin County |
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| Williamstown |
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vs. Owen County |
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| Dec 8, 2008 |
| Barbourville |
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vs. Harlan |
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| Lyon County |
- |
vs. Dawson Springs |
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| Owensboro Catholic |
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vs. Trinity (Whitesville) |
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| Paintsville |
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vs. Riverside Christian |
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| Rowan County |
- |
vs. Menifee County |
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| Dec 9, 2008 |
| Adair County |
- |
vs. Marion County |
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| Augusta |
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vs. Bracken County |
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| Bardstown |
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vs. Fort Knox |
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| Barren County |
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vs. Allen County-Scottsville |
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| Beechwood |
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vs. Dayton |
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| Belfry |
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vs. Pikeville |
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| Bellevue |
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vs. Silver Grove |
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| Berea |
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vs. Paris |
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| Betsy Layne |
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vs. Paintsville |
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| Bishop Brossart |
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