| 1999 |
| | Date | Site | Opponent | Score | Record |
| 08/21/1999 | H | Christian County | 47-7 | 1-0-0 | |
| 08/28/1999 | Scott County High School | Lexington Catholic | 0-35 | 1-1-0 | |
| 09/03/1999 | A | Greenwood | 35-0 | 2-1-0 | |
| 09/10/1999 | H | Warren Central* | 28-6 | 3-1-0, (1-0-0) | |
| 09/17/1999 | H | Logan County* | 52-0 | 4-1-0, (2-0-0) | |
| 09/24/1999 | H | Franklin-Simpson* | 13-14 | 4-2-0, (2-1-0) | |
| 10/01/1999 | A | Louisville Butler | 18-0 | 5-2-0 | |
| 10/15/1999 | H | Allen County-Scottsville* | 48-7 | 6-2-0, (3-1-0) | |
| 10/22/1999 | A | Owensboro Senior* | 14-17 2OT | 6-3-0, (3-2-0) | |
| 10/29/1999 | A | Warren East* | 38-15 | 7-3-0, (4-2-0) | |
| 11/05/1999 | A | Union County | 20-12 | 8-3-0 | |
| (Region Quarterfinals) | |||||
| 11/12/1999 | A | Franklin-Simpson* | 0-14 | 8-4-0, (4-3-0) | |
| (Region Semifinals) | |||||
| | Coach Kevin Wallace | PF - 313 PA - 127 | |||
| | 3A, Region One, District Two | ||||
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| Previous Season: 1998 |
| Next Season: 2000 |
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