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Covington Holmes |
| | Date | Site | Winner | Score | Record |
| 03/24/1978 | Freedom Hall | Covington Holmes | 71-83 | 0-1 | |
| (Sweet 16 Quarterfinals) | |||||
| 12/23/1989 | Louisville Fairdale | Covington Holmes | 53-81 | 0-2 (Covington Holmes has won 2 straight) | |
| 01/19/2008 | West Jessamine | Covington Holmes | 59-69 | 0-3 (Covington Holmes has won 3 straight) | |
| 01/04/2020 | South Oldham | Bowling Green | 75-66 | 1-3 | |
| Bowling Green longest streak: 1 straight | Covington Holmes longest streak: 3 straight | |||