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Calloway County |
| | Date | Site | Winner | Score | Record |
| 11/07/1997 | Warren East | Calloway County | 0-24 | 0-1-0 | |
| (Region Quarterfinals) | |||||
| 11/02/2012 | Warren East | Warren East | 49-7 | 1-1-0 | |
| (Region Quarterfinals) | |||||
| 11/08/2013 | Warren East | Warren East | 21-0 | 2-1-0 (Warren East has won 2 straight) | |
| (Region Quarterfinals) | |||||
| 11/07/2014 | Warren East | Warren East | 38-0 | 3-1-0 (Warren East has won 3 straight) | |
| (Region Quarterfinals) | |||||
| 09/15/2023 | Calloway County | Warren East | 51-20 | 4-1-0 (Warren East has won 4 straight) | |
| 09/20/2024 | Warren East | Warren East | 68-0 | 5-1-0 (Warren East has won 5 straight) | |
| Warren East longest streak: 5 straight | Calloway County longest streak: 1 straight | |||