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Owensboro Senior |
| | Date | Site | Winner | Score | Record |
| 03/17/1972 | Freedom Hall | Owensboro Senior | 59-70 | 0-1 | |
| (Sweet 16 Quarterfinals) | |||||
| 01/22/1976 | Owensboro Senior | Owensboro Senior | 61-90 | 0-2 (Owensboro Senior has won 2 straight) | |
| 02/11/1977 | Warren East | Warren East | 74-55 | 1-2 | |
| 03/19/1986 | Rupp Arena | Owensboro Senior | 47-54 | 1-3 | |
| (Sweet 16 First Round) | |||||
| 12/22/2010 | Warren East | Owensboro Senior | 55-71 | 1-4 (Owensboro Senior has won 2 straight) | |
| 12/28/2012 | McLean County | Warren East | 74-70 OT | 2-4 | |
| 12/21/2023 | South Warren | Warren East | 72-68 | 3-4 (Warren East has won 2 straight) | |
| Warren East longest streak: 2 straight | Owensboro Senior longest streak: 2 straight | |||