| 2020 |
| Fri., Nov. 6 | @ Page | W 43-7 | 1st Round Playoffs | | Fri., Nov. 13 | vs. Beech | L 0-36 | 2nd Round Playoffs |
| 2019 |
| Fri., Nov. 8 | @ Shelbyville | L 0-39 | 1st Round Playoffs |
| 2018 |
| Fri., Nov. 2 | vs. Lincoln County | W 48-7 | 1st Round Playoffs | | Fri., Nov. 9 | vs. Shelbyville | W 48-20 | 2nd Round Playoffs | | Fri., Nov. 16 | Beech | L 19-20 | 3rd Round Playoffs |
| 2017 |
| Fri., Nov. 3 | @ Shelbyville | W 47-12 | 1st Round Playoffs | | Fri., Nov. 10 | @ Beech | L 3-10 | 2nd Round Playoffs |
| 2016 |
| Fri., Nov. 4 | vs. Stewarts Creek | W 41-7 | 1st Round Playoffs | | Fri., Nov. 11 | @ Independence | L 20-42 | 2nd Round Playoffs |
| 2015 |
| Fri., Nov. 6 | vs. LaVergne | W 26-7 | 1st Round Playoffs | | Fri., Nov. 13 | vs. Beech | W 42-7 | 2nd Round Playoffs | | Fri., Nov. 20 | @ Independence | L 20-28 | 3rd Round Playoffs |
| 2014 |
| Fri., Nov. 7 | vs. Kenwood | W 55-12 | 1st Round Playoffs | | Fri., Nov. 14 | vs. Springfield | W 41-7 | 2nd Round Playoffs | | Fri., Nov. 21 | vs. Shelbyville | W 42-9 | 3rd Round Playoffs | | Fri., Nov. 28 | @ Ridgeway | W 35-7 | Semi-finals Playoffs | | Fri., Dec. 5 | West | L 6-23 | Championship Game @ Cookeville |
| 2013 |
| Fri., Nov. 8 | @ Beech | W 31-26 | 1st Round Playoffs | | Fri., Nov. 15 | vs. Northeast | L 21-31 | 2nd Round Playoffs |
| 2012 |
| Fri., Nov. 2 | @ Antioch | W 17-12 | 1st Round Playoffs | | Fri., Nov. 9 | @ Beech | L 6-35 | 2nd Round Playoffs |
| 2009 |
| Fri., Nov. 6 | @ Glencliff | W 20-17 | 1st Round Playoffs | | Fri., Nov. 13 | @ Columbia Central | L 21-35 | 2nd Round Playoffs |
| 2008 |
| Fri., Nov. 7 | vs. Clarksville | W 49-14 | 1st Round Playoffs | | Fri., Nov. 14 | vs. Mt. Juliet | W 49-13 | 2nd Round Playoffs | | Fri., Nov. 21 | @ Beech | W 42-21 | 3rd Round Playoffs | | Fri., Nov. 28 | vs. Henry County | W 31-24 | Semi-finals Playoffs | | Sat., Dec. 6 | Maryville | W 10-7 | Championship Game |
| 2007 |
| Fri., Nov. 9 | vs. Mt. Juliet | W 44-20 | 1st Round Playoffs | | Fri., Nov. 16 | vs. Maplewood | L 17-18 | 2nd Round Playoffs |
| 2006 |
| Fri., Nov. 3 | vs. Rossview | W 42-3 | 1st Round Playoffs | | Fri., Nov. 10 | vs. Mt. Juliet | W 28-21 | 2nd Round Playoffs | | Fri., Nov. 17 | @ Clarksville | W 41-3 | 3rd Round Playoffs | | Fri., Nov. 24 | @ Henry County | W 42-7 | Semi-finals Playoffs | | Sat., Dec. 2 | Maryville | L 10-35 | Championship Game |
| 2005 |
| Fri., Nov. 4 | vs. Portland | W 42-0 | 1st Round Playoffs | | Fri., Nov. 11 | vs. Maplewood | W 21-7 | 2nd Round Playoffs | | Fri., Nov. 18 | vs. Whites Creek | W 31-7 | 3rd Round Playoffs | | Fri., Nov. 25 | vs. Melrose | L 7-28 | Semi-finals Playoffs |
| 2004 |
| Fri., Nov. 5 | @ Stratford | L 13-19 | 1st Round Playoffs |
| 2003 |
| Fri., Nov. 7 | vs. White House | W 42-14 | 1st Round Playoffs | | Fri., Nov. 14 | vs. Shelbyville | W 60-7 | 2nd Round Playoffs | | Fri., Nov. 21 | vs. Stratford | W 16-6 | 3rd Round Playoffs | | Fri., Nov. 28 | vs. Melrose | W 27-26 | Semi-finals Playoffs | | Sat., Dec. 6 | Morristown West | W 21-0 | Championship Game @ Murfreesboro |
| 2002 |
| Fri., Nov. 8 | vs. Whites Creek | W 51-0 | 1st Round Playoffs | | Fri., Nov. 15 | vs. Tullahoma | W 42-12 | 2nd Round Playoffs | | Fri., Nov. 22 | vs. John Overton | W 17-0 | 3rd Round Playoffs | | Fri., Nov. 29 | @ Melrose | W 7-6 | Semi-finals Playoffs | | Sat., Dec. 7 | Maryville | L 26-29 | Championship Game @ Murfreesboro |
| 2001 |
| Fri., Nov. 2 | vs. Whites Creek | W 42-0 | 1st Round Playoffs | | Fri., Nov. 9 | @ Pearl-Cohn | W 30-13 | 2nd Round Playoffs | | Fri., Nov. 16 | @ White House | W 34-10 | 3rd Round Playoffs | | Sat., Nov. 24 | vs. Memphis East | W 10-6 | Semi-finals Playoffs | | Sat., Dec. 1 | Maryville | L 27-34 | Championship Game |
| 2000 |
| | Northwest | W 43-7 | 1st Round Playoffs | | | Clarksville | W 28-0 | 2nd Round Playoffs | | | Smyrna | W 19-13 | 3rd Round Playoffs | | | Memphis East | L 15-44 | Semi-finals Playoffs |
| 1999 |
| | Stratford | W 36-6 | 1st Round Playoffs | | | Whites Creek | L 7-27 | 2nd Round Playoffs |
| 1998 |
| | Hendersonville | L 23-54 | 1st Round Playoffs |
| 1997 |
| | Brentwood | L 21-31 | 1st Round Playoffs |
| 1989 |
| | Stratford | W 21-14 | 1st Round Playoffs | | | Gallatin | L 0-24 | 2nd Round Playoffs |
|
| Hillsboro Playoff Totals |
| Record |
45-21-0 1836-1086 |
| Home Record | 26-4 |
| Away Record | 12-7 |
|
