| 2020 |
| Fri., Nov. 6 | @ Springfield | L 7-42 | 1st Round Playoffs |
| 2019 |
| Fri., Nov. 8 | @ Springfield | L 21-42 | 1st Round Playoffs |
| 2018 |
| Fri., Nov. 2 | vs. Creek Wood | W 16-14 | 1st Round Playoffs | | Fri., Nov. 9 | @ Springfield | L 6-13 | 2nd Round Playoffs |
| 2017 |
| Fri., Nov. 3 | vs. Greenbrier | W 21-7 | 1st Round Playoffs | | Fri., Nov. 10 | @ White House | W 30-7 | 2nd Round Playoffs | | Fri., Nov. 17 | vs. Springfield | L 22-23 | 3rd Round Playoffs |
| 2012 |
| Fri., Nov. 2 | @ Lexington | L 6-42 | 1st Round Playoffs |
| 2009 |
| | David Lipscomb | L 8-28 | 1st Round Playoffs |
| 2008 |
| | Page | L 7-10 | 1st Round Playoffs |
| 2007 |
| | Marshall County | L 14-21 | 1st Round Playoffs |
| 2006 |
| | Cheatham County | W 42-35 | 1st Round Playoffs | | | Giles County | L 7-21 | 2nd Round Playoffs |
| 2005 |
| | Creek Wood | L 20-33 | 1st Round Playoffs |
| 2004 |
| | Montgomery Central | W 49-0 | 1st Round Playoffs | | | Crockett County | W 28-17 | 2nd Round Playoffs | | | Greenbrier | L 7-14 | 3rd Round Playoffs |
| 2003 |
| | Sycamore | L 34-37 | 1st Round Playoffs |
| 2002 |
| | Marshall County | L 13-28 | 1st Round Playoffs |
| 2001 |
| | Marshall County | W 29-21 | 1st Round Playoffs | | | Crockett County | L 7-9 | 2nd Round Playoffs |
| 2000 |
| | Page | W 21-14 | 1st Round Playoffs | | | Milan | W 29-22 | 2nd Round Playoffs | | | Marshall County | W 7-6 | 3rd Round Playoffs | | | Covington | L 8-28 | Semi-finals Playoffs |
| 1999 |
| | Giles County | W 35-6 | 1st Round Playoffs | | | Page | W 25-0 | 2nd Round Playoffs | | | Milan | L 8-29 | 3rd Round Playoffs |
| 1997 |
| | Ridgeway | L 43-44 | 1st Round Playoffs |
| 1996 |
| | Father Ryan | L 7-28 | 1st Round Playoffs |
| 1988 |
| | Milan | L 9-13 | 1st Round Playoffs |
| 1985 |
| | Milan | L 7-34 | 1st Round Playoffs |
| 1978 |
| | Milan | W 21-0 | 2nd Round Playoffs | | | Brentwood Academy | L 0-24 | 3rd Round Playoffs |
|
| Jackson South Side Playoff Totals |
| Record |
13-21-0 614-712 |
| Home Record | 2-1 |
| Away Record | 1-4 |
|
