| 2020 |
| Fri., Oct. 2 | @ Covington | W 14-7 (3OT) | R |
| 2017 |
| Fri., Aug. 25 | @ Peabody | L 21-27 (OT) | R | | Fri., Sep. 15 | vs. Covington | L 27-28 (OT) | R |
| 2013 |
| Fri., Oct. 25 | vs. Huntingdon | L 20-21 (OT) | R |
| 2012 |
| Fri., Aug. 17 | @ Peabody | W 36-35 (OT) | R |
| 2006 |
| Fri., Nov. 17 | @ Humboldt | W 14-13 (OT) | 3rd Round Playoffs |
| 2004 |
| Fri., Nov. 5 | @ Mitchell | W 23-20 (OT) | 1st Round Playoffs |
| 2001 |
| Fri., Oct. 26 | vs. Humboldt | L 20-26 (OT) | R |
| 1997 |
| Fri., Sep. 12 | vs. Peabody | W 17-14 (OT) | R |
| 1996 |
| Fri., Aug. 30 | vs. Jackson North Side | W 10-7 (2OT) | R |
| 1994 |
| Fri., Oct. 28 | vs. Huntingdon | W 22-21 (OT) | R |
| 1991 |
| Fri., Oct. 25 | @ Huntingdon | W 17-14 (OT) | R |
| 1986 |
| Fri., Oct. 17 | vs. Union City | W 9-6 (OT) | R |
| 1982 |
| Fri., Sep. 3 | vs. Dyersburg | W 7-0 (OT) | R |
| 1978 |
| Fri., Aug. 25 | vs. Dyersburg | W 14-13 (OT) | R |
|
| Milan Overtime Totals |
| Record |
11-4-0 271-252 |
| Home Record | 6-3 |
| Away Record | 5-1 |
|
