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Owensboro Senior |
| | Date | Site | Winner | Score | Record |
| 11/16/2018 | South Warren | South Warren | 44-7 | 1-0-0 | |
| (Region Finals) | |||||
| 11/10/2023 | Owensboro Senior | Owensboro Senior | 22-53 | 1-1-0 | |
| (Region Semifinals) | |||||
| South Warren longest streak: 1 straight | Owensboro Senior longest streak: 1 straight | |||