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Breckinridge County |
| | Date | Site | Winner | Score | Record |
| 01/23/1970 | Warren East | Warren East | 98-66 | 1-0 | |
| 12/04/1987 | Breckinridge County | Warren East | 72-63 | 2-0 (Warren East has won 2 straight) | |
| 12/02/1988 | Warren East | Warren East | 63-56 OT | 3-0 (Warren East has won 3 straight) | |
| 12/01/1989 | Breckinridge County | Breckinridge County | 56-67 | 3-1 | |
| 12/01/1990 | Warren East | Warren East | 74-68 | 4-1 | |
| 12/06/1991 | Breckinridge County | Breckinridge County | 55-63 | 4-2 | |
| 12/04/1992 | Warren East | Warren East | 53-45 | 5-2 | |
| 12/03/1993 | Breckinridge County | Warren East | 63-50 | 6-2 (Warren East has won 2 straight) | |
| 12/02/1994 | Warren East | Breckinridge County | 47-60 | 6-3 | |
| 12/23/1998 | McLean County | Breckinridge County | 35-62 | 6-4 (Breckinridge County has won 2 straight) | |
| 12/27/2008 | Grayson County | Warren East | 73-62 | 7-4 | |
| 12/21/2022 | Ohio County | Breckinridge County | 48-69 | 7-5 | |
| Warren East longest streak: 3 straight | Breckinridge County longest streak: 2 straight | |||