| 2019 |
| Fri., Nov. 8 | @ Forrest | L 7-37 | 1st Round Playoffs |
| 2018 |
| Fri., Nov. 2 | @ Columbia Academy | L 6-24 | 1st Round Playoffs |
| 2017 |
| Fri., Nov. 3 | @ Columbia Academy | L 10-49 | 1st Round Playoffs |
| 2014 |
| Fri., Nov. 7 | @ Manassas | W 27-25 | 1st Round Playoffs | | Fri., Nov. 14 | @ Waverly | W 51-30 | 2nd Round Playoffs | | Fri., Nov. 21 | @ Milan | L 0-38 | 3rd Round Playoffs |
| 2013 |
| Fri., Nov. 8 | vs. South Gibson | W 34-20 | 1st Round Playoffs | | Fri., Nov. 15 | @ Westview | L 0-32 | 2nd Round Playoffs |
| 2012 |
| Fri., Nov. 2 | vs. Lewis County | W 35-34 | 1st Round Playoffs | | Fri., Nov. 9 | vs. East Hickman | W 13-7 | 2nd Round Playoffs | | Fri., Nov. 16 | @ Milan | L 6-35 | 3rd Round Playoffs |
| 2011 |
| | Fairview | L 0-42 | 1st Round Playoffs |
| 2008 |
| | CPA | L 19-47 | 1st Round Playoffs |
| 2007 |
| | Stewart County | W 51-20 | 1st Round Playoffs | | | Lewis County | W 21-14 | 2nd Round Playoffs | | | Goodpasture | L 12-35 | 3rd Round Playoffs |
| 1998 |
| | Bolivar Central | L 16-22 | 1st Round Playoffs |
| 1997 |
| | McNairy Central | L 6-24 | 1st Round Playoffs |
| 1996 |
| | Portland | L 0-21 | 1st Round Playoffs |
| 1995 |
| | White House | L 13-34 | 1st Round Playoffs |
| 1990 |
| | White House | L 13-34 | 1st Round Playoffs |
| 1987 |
| | Portland | W 9-0 | 1st Round Playoffs | | | Brentwood Academy | L 14-28 | 2nd Round Playoffs |
| 1986 |
| | White House | L 6-7 | 1st Round Playoffs |
| 1980 |
| | Brentwood Academy | L 0-28 | 2nd Round Playoffs |
| 1977 |
| | Brentwood Academy | L 6-7 | 2nd Round Playoffs |
|
| Hickman County Playoff Totals |
| Record |
8-18-0 375-694 |
| Home Record | 3-0 |
| Away Record | 2-6 |
|
