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Monroe County |
| | Date | Site | Winner | Score | Record |
| 09/08/1995 | Monroe County | Monroe County | 13-16 | 0-1-0 | |
| 09/13/1996 | Greenwood | Greenwood | 28-16 | 1-1-0 | |
| 09/12/1997 | Monroe County | Greenwood | 34-0 | 2-1-0 (Greenwood has won 2 straight) | |
| 09/11/1998 | Greenwood | Monroe County | 3-6 | 2-2-0 | |
| 09/28/2007 | Greenwood | Greenwood | 21-0 | 3-2-0 | |
| 10/03/2008 | Monroe County | Greenwood | 35-21 | 4-2-0 (Greenwood has won 2 straight) | |
| Greenwood longest streak: 2 straight | Monroe County longest streak: 1 straight | |||