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Monroe County |
| | Date | Site | Winner | Score | Record |
| 10/06/2011 | Monroe County | Monroe County | 10-42 | 0-1-0 | |
| 10/04/2012 | South Warren | Monroe County | 0-41 | 0-2-0 (Monroe County has won 2 straight) | |
| 11/16/2012 | Monroe County | Monroe County | 10-20 | 0-3-0 (Monroe County has won 3 straight) | |
| (Region Finals) | |||||
| 10/18/2013 | Monroe County | South Warren | 53-8 | 1-3-0 | |
| 10/17/2014 | South Warren | South Warren | 49-14 | 2-3-0 (South Warren has won 2 straight) | |
| 08/20/2016 | Western Kentucky University | South Warren | 56-14 | 3-3-0 (South Warren has won 3 straight) | |
| South Warren longest streak: 3 straight | Monroe County longest streak: 3 straight | |||