| 2019 |
| Fri., Nov. 8 | @ Briarcrest | W 35-33 | 3rd Round Playoffs | | Fri., Nov. 15 | @ McCallie | L 27-35 | Semi-finals Playoffs |
| 2018 |
| Fri., Nov. 2 | vs. Father Ryan | W 14-13 | 1st Round Playoffs | | Fri., Nov. 9 | @ McCallie | L 14-27 | 2nd Round Playoffs |
| 2017 |
| Fri., Nov. 3 | vs. Baylor | L 20-28 | 1st Round Playoffs |
| 2016 |
| Fri., Nov. 11 | @ Briarcrest | W 49-21 | 3rd Round Playoffs | | Fri., Nov. 18 | @ MBA | L 17-21 | Semi-finals Playoffs |
| 2015 |
| Fri., Nov. 6 | vs. Father Ryan | W 29-19 | 1st Round Playoffs | | Fri., Nov. 13 | @ Christian Brothers | L 17-30 | 2nd Round Playoffs |
| 2014 |
| Fri., Nov. 14 | vs. Briarcrest | W 42-6 | 3rd Round Playoffs | | Fri., Nov. 21 | vs. MUS | W 27-24 | Semi-finals Playoffs | | Thu., Dec. 4 | MBA | L 7-10 | Championship Game @ Cookeville |
| 2013 |
| Fri., Nov. 15 | vs. Christian Brothers | W 40-11 | 3rd Round Playoffs | | Fri., Nov. 22 | vs. Brentwood Academy | W 21-12 | Semi-finals Playoffs | | Thu., Dec. 5 | MUS | W 27-10 | Championship Game @ Cookeville |
| 2012 |
| Fri., Nov. 9 | vs. McCallie | W 37-7 | 3rd Round Playoffs | | Fri., Nov. 16 | vs. MBA | W 35-7 | Semi-finals Playoffs | | Thu., Nov. 29 | vs. MUS | W 31-14 | Championship Game |
| 2011 |
| | Father Ryan | W 42-17 | 1st Round Playoffs | | | MUS | W 28-0 | Semi-finals Playoffs | | | Baylor | W 48-10 | Championship Game |
| 2010 |
| | MBA | W 35-14 | 1st Round Playoffs | | | Brentwood Academy | W 20-19 | Semi-finals Playoffs | | | Baylor | W 28-21 | Championship Game |
| 2009 |
| | MBA | L 24-27 | 1st Round Playoffs |
| 2008 |
| | McCallie | W 34-17 | 1st Round Playoffs | | | Brentwood Academy | L 24-27 | Semi-finals Playoffs |
| 2007 |
| | Christian Brothers | W 34-27 | 1st Round Playoffs | | | Brentwood Academy | L 13-42 | Semi-finals Playoffs |
|
| Ensworth Playoff Totals |
| Record |
20-9-0 819-549 |
| Home Record | 9-1 |
| Away Record | 2-4 |
|
