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Owensboro Senior |
| | Date | Site | Winner | Score | Record |
| 12/14/2002 | Greenwood | Owensboro Senior | 64-65 | 0-1 | |
| 12/19/2007 | Bowling Green | Greenwood | 60-50 | 1-1 | |
| 12/01/2012 | South Warren | Owensboro Senior | 62-65 | 1-2 | |
| 12/21/2016 | Owensboro Senior | Owensboro Senior | 71-72 | 1-3 (Owensboro Senior has won 2 straight) | |
| 01/08/2022 | Bowling Green | Greenwood | 73-54 | 2-3 | |
| 01/06/2024 | Bowling Green | Owensboro Senior | 50-67 | 2-4 | |
| Greenwood longest streak: 1 straight | Owensboro Senior longest streak: 2 straight | |||