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Portland (TN) |
| | Date | Site | Winner | Score | Record |
| 12/04/1997 | Greenwood | Greenwood | 72-57 | 1-0 | |
| 12/03/1998 | Portland (TN) | Portland (TN) | 53-60 | 1-1 | |
| 12/02/1999 | Greenwood | Greenwood | 73-58 | 2-1 | |
| 11/30/2000 | Portland (TN) | Portland (TN) | 29-57 | 2-2 | |
| 12/27/2024 | Franklin-Simpson | Greenwood | 84-62 | 3-2 | |
| Greenwood longest streak: 1 straight | Portland (TN) longest streak: 1 straight | |||