| # | Date | Teams | # of OTs | Game # | Comments |
| 1 | Saturday, February 2, 1924 |
Batesville 18 Moores Hill 13 |
1 | 16 | . |
| 2 | Saturday, January 23, 1926 |
Holton 28 Osgood 25 |
2 | 33 | each OT was 5 minutes long |
| 3 | Saturday, January 25, 1930 |
New Marion 39 Sunman 35 |
1 | 37 | . |
| 4 | Saturday, January 24, 1931 |
Sunman 23 Napoleon 22 |
1 | 44 | . |
| 5 | Saturday, January 21, 1933 |
Versailles 39 New Marion 34 |
1 | 61 | . |
| 6 | 1937 |
Milan 30 Osgood 29 |
1 | 93 | . |
| 7 | 1938 |
Holton 35 Sunman 33 |
1 | 102 | championship |
| 8 | 1942 |
Osgood 40 Milan 38 |
2 | 129 | . |
| 9 | 1942 |
Osgood 40 Napoleon 37 |
1 | 130 | championship |
| 10 | 1947 |
Cross Plains 49 New Marion 48 |
1 | 160 | . |
| 11 | 1958 |
Milan 33 Versailles 30 |
2 | 240 | . |
| 12 | 1962 |
New Marion 47 Cross Plains 44 |
2 | 264 | . |
| 13 | 1962 |
Versailles 53 New Marion 51 |
1 | 268 | . |
| 14 | 1963 |
Batesville 63 Holton 60 |
4* | 275 | . |
| 15 | 1964 |
Jac-Cen-Del 59 Holton 58 |
1 | 284 | championship |
| * indicates current record |
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