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Madisonville-North Hopkins |
| | Date | Site | Winner | Score | Record |
| 01/17/1992 | Madisonville-North Hopkins | Greenwood | 80-78 OT | 1-0 | |
| 01/15/1993 | Greenwood | Madisonville-North Hopkins | 41-67 | 1-1 | |
| 01/04/2003 | Daviess County | Madisonville-North Hopkins | 52-69 | 1-2 (Madisonville-North Hopkins has won 2 straight) | |
| 12/20/2004 | Daviess County | Greenwood | 60-56 | 2-2 | |
| 01/07/2023 | Bowling Green | Madisonville-North Hopkins | 58-69 | 2-3 | |
| Greenwood longest streak: 1 straight | Madisonville-North Hopkins longest streak: 2 straight | |||