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Grayson County |
| | Date | Site | Winner | Score | Record |
| 12/13/1996 | Greenwood | Greenwood | 66-56 | 1-0 | |
| 12/13/1997 | Greenwood | Greenwood | 60-51 | 2-0 (Greenwood has won 2 straight) | |
| 12/21/2011 | Central Hardin | Grayson County | 39-47 | 2-1 | |
| 12/26/2013 | Edmonson County | Greenwood | 67-57 | 3-1 | |
| 12/22/2018 | Edmonson County | Greenwood | 39-34 | 4-1 (Greenwood has won 2 straight) | |
| 02/16/2024 | Greenwood | Grayson County | 62-70 | 4-2 | |
| 02/11/2025 | Grayson County | Grayson County | 65-67 | 4-3 (Grayson County has won 2 straight) | |
| Greenwood longest streak: 2 straight | Grayson County longest streak: 2 straight | |||