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Rich Pond |
| | Date | Site | Winner | Score | Record |
| 03/02/1929 | Smiths Grove | Rich Pond | 16-19 | 0-1 | |
| (10th District Semifinals) | |||||
| 03/02/1933 | Western Kentucky State Teachers College | Bowling Green | 32-13 | 1-1 | |
| (19th District First Round) | |||||
| 03/03/1942 | Bowling Green | Bowling Green | 27-25 | 2-1 (Bowling Green has won 2 straight) | |
| (17th District Quarterfinals) | |||||
| Bowling Green longest streak: 2 straight | Rich Pond longest streak: 1 straight | |||