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Hopkinsville |
| | Date | Site | Winner | Score | Record |
| 12/11/1999 | Greenwood | Greenwood | 77-75 | 1-0 | |
| 12/28/2006 | Franklin-Simpson | Greenwood | 55-36 | 2-0 (Greenwood has won 2 straight) | |
| 12/02/2014 | Hopkinsville | Hopkinsville | 45-82 | 2-1 | |
| 12/01/2015 | Greenwood | Hopkinsville | 62-81 | 2-2 (Hopkinsville has won 2 straight) | |
| 01/13/2020 | Greenwood | Greenwood | 61-48 | 3-2 | |
| 01/20/2021 | Greenwood | Greenwood | 74-62 | 4-2 (Greenwood has won 2 straight) | |
| Greenwood longest streak: 2 straight | Hopkinsville longest streak: 2 straight | |||