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| 09-09-99 |
Menifee County |
Away | 41 - 22 - W |
| 09-14-99 | Bath County | Home | 64 - 11 - W |
| 09-16-99 | Bracken County | Away | 45 - 11 - W |
| 09-18-99 | East Carter | Away | 49 - 23 - W |
| 09-21-99 | Fleming County | Away | 31 - 14 - W |
| 09-23-99 | Mason County | Home | 49 - 21 - W |
| 09-27-99 | St Pat | Away | 40 - 23 - W |
| 09-30-99 | Bath County | Away | 41 - 20 - W |
| 10-05-99 | Bracken County | Home | 41 - 10 - W |
| 10-07-99 | Mason County | Away | 33 - 15 - W |
| 10-09-99 | East Carter | Home | CANCELLED |
| 10-12-99 | Fleming County | Home | 48 - 35 - W |
| 10-14-99 | St Pat | Home | 38 - 26 - W |
| 10-20-99 | ORVMSC Tournament | Bracken | 36 - 21 - W |
| 10-23-99 | ORVMSC Tournament | Fleming | 29 - 21 - W |
| 10-25-99 | 61st District Tournament | Morgan | 42 - 11 - W |
| 10-27-99 | 61st District Tournament | Menifee | 53 - 24 - W |
| 10-28-99 | Menifee County | Home | 43 - 21 - W |
| 11-04-99 | Morgan County | Home | W |