| 2020 |
| Fri., Nov. 6 | vs. Cane Ridge | W 45-13 | 1st Round Playoffs | | Fri., Nov. 13 | @ Independence | W 31-28 | 2nd Round Playoffs | | Fri., Nov. 20 | vs. Franklin | W 55-34 | 3rd Round Playoffs | | Fri., Nov. 27 | @ Bartlett | W 24-14 | Semi-finals Playoffs | | Sat., Dec. 5 | Oakland | L 33-56 | Championship Game |
| 2019 |
| Fri., Nov. 8 | vs. McGavock | W 38-6 | 1st Round Playoffs | | Fri., Nov. 15 | vs. Independence | W 20-13 | 2nd Round Playoffs | | Fri., Nov. 22 | vs. Ravenwood | L 6-34 | 3rd Round Playoffs |
| 2018 |
| Fri., Nov. 2 | vs. McGavock | W 31-11 | 1st Round Playoffs | | Fri., Nov. 9 | vs. Independence | W 27-24 | 2nd Round Playoffs | | Fri., Nov. 16 | vs. Ravenwood | L 24-47 | 3rd Round Playoffs |
| 2017 |
| Fri., Nov. 3 | vs. McGavock | W 36-7 | 1st Round Playoffs | | Fri., Nov. 10 | @ Cane Ridge | L 13-28 | 2nd Round Playoffs |
| 2016 |
| Fri., Nov. 4 | vs. Kirby | W 55-28 | 1st Round Playoffs | | Fri., Nov. 11 | @ Memphis Central | W 34-27 (OT) | 2nd Round Playoffs | | Fri., Nov. 18 | @ Centennial | W 24-21 | 3rd Round Playoffs | | Fri., Nov. 25 | vs. Independence | L 24-27 | Semi-finals Playoffs |
| 2015 |
| Fri., Nov. 6 | @ Memphis Central | W 52-7 | 1st Round Playoffs | | Fri., Nov. 13 | @ Centennial | L 7-25 | 2nd Round Playoffs |
| 2012 |
| Fri., Nov. 2 | vs. Wilson Central | W 35-0 | 1st Round Playoffs | | Fri., Nov. 9 | vs. John Overton | W 34-14 | 2nd Round Playoffs | | Fri., Nov. 16 | vs. Mt. Juliet | L 20-31 | 3rd Round Playoffs |
| 2011 |
| Fri., Nov. 4 | @ Independence | W 10-7 | 1st Round Playoffs | | Fri., Nov. 11 | @ Franklin | W 23-14 | 2nd Round Playoffs | | Fri., Nov. 18 | @ Mt. Juliet | L 21-34 | 3rd Round Playoffs |
| 2010 |
| Fri., Nov. 5 | @ Smyrna | L 16-38 | 1st Round Playoffs |
| 2009 |
| Fri., Nov. 6 | vs. Rossview | W 35-7 | 1st Round Playoffs | | Fri., Nov. 13 | vs. Dickson County | W 31-0 | 2nd Round Playoffs | | Fri., Nov. 20 | vs. Franklin | W 21-20 | 3rd Round Playoffs | | Fri., Nov. 27 | vs. White Station | L 27-31 | Semi-finals Playoffs |
| 2008 |
| Fri., Nov. 7 | vs. Antioch | W 44-6 | 1st Round Playoffs | | Fri., Nov. 14 | vs. Centennial | W 21-7 | 2nd Round Playoffs | | Fri., Nov. 21 | vs. Franklin | L 7-14 | 3rd Round Playoffs |
| 2007 |
| Fri., Nov. 9 | @ Hunters Lane | L 10-14 | 1st Round Playoffs |
| 2006 |
| Fri., Nov. 3 | @ Hunters Lane | L 23-26 | 1st Round Playoffs |
| 2005 |
| Fri., Nov. 4 | vs. McGavock | W 31-6 | 1st Round Playoffs | | Fri., Nov. 11 | @ Gallatin | W 10-9 | 2nd Round Playoffs | | Fri., Nov. 18 | @ Ravenwood | L 7-16 | 3rd Round Playoffs |
| 2004 |
| Fri., Nov. 5 | vs. Hunters Lane | W 13-12 | 1st Round Playoffs | | Fri., Nov. 12 | vs. Ravenwood | W 30-27 | 2nd Round Playoffs | | Fri., Nov. 19 | vs. Franklin | L 7-14 | 3rd Round Playoffs |
| 2003 |
| Fri., Nov. 7 | vs. Glencliff | W 28-2 | 1st Round Playoffs | | Fri., Nov. 14 | vs. Franklin | L 10-27 | 2nd Round Playoffs |
| 2002 |
| Fri., Nov. 8 | vs. Hunters Lane | W 12-7 | 1st Round Playoffs | | Sat., Nov. 16 | vs. Dickson County | W 14-7 | 2nd Round Playoffs | | Fri., Nov. 22 | vs. Franklin | W 19-14 | 3rd Round Playoffs | | Fri., Nov. 29 | @ Germantown | W 24-14 | Semi-finals Playoffs | | Sat., Dec. 7 | Riverdale | W 10-7 | Championship Game @ Murfreesboro |
| 2001 |
| Fri., Nov. 2 | vs. Beech | W 28-14 | 1st Round Playoffs | | Fri., Nov. 9 | vs. Gallatin | L 20-22 | 2nd Round Playoffs |
| 2000 |
| | Henry County | W 48-19 | 1st Round Playoffs | | | Antioch | W 29-0 | 2nd Round Playoffs | | | Riverdale | L 6-21 | 3rd Round Playoffs |
| 1999 |
| | Antioch | L 18-35 | 1st Round Playoffs |
| 1998 |
| | Henry County | W 52-24 | 1st Round Playoffs | | | Dickson County | W 23-19 | 2nd Round Playoffs | | | Hendersonville | L 23-33 | 3rd Round Playoffs |
| 1997 |
| | Hillsboro | W 31-21 | 1st Round Playoffs | | | Hendersonville | W 28-7 | 2nd Round Playoffs | | | Mt. Juliet | L 21-23 | 3rd Round Playoffs |
| 1994 |
| | Powell | L 21-35 | 1st Round Playoffs |
| 1993 |
| | Powell | L 20-28 | 1st Round Playoffs |
|
| Brentwood Playoff Totals |
| Record |
39-23-0 1540-1176 |
| Home Record | 23-9 |
| Away Record | 9-7 |
|