| 2020 |
| Fri., Nov. 6 | @ Marion County | L 17-35 | 1st Round Playoffs |
| 2019 |
| Fri., Nov. 8 | @ Tyner Academy | L 0-54 | 1st Round Playoffs |
| 2018 |
| Fri., Nov. 2 | @ Polk County | W 14-7 | 1st Round Playoffs | | Fri., Nov. 9 | @ Watertown | L 6-40 | 2nd Round Playoffs |
| 2017 |
| Fri., Nov. 3 | @ Marion County | L 7-28 | 1st Round Playoffs |
| 2016 |
| Fri., Nov. 4 | @ Marion County | L 0-42 | 1st Round Playoffs |
| 2015 |
| Fri., Nov. 6 | @ Marion County | L 0-42 | 1st Round Playoffs |
| 2014 |
| Fri., Nov. 7 | vs. Fairview | W 35-6 | 1st Round Playoffs | | Fri., Nov. 14 | @ Christ Presbyterian | L 29-48 | 2nd Round Playoffs |
| 2013 |
| Fri., Nov. 8 | vs. East Hickman | W 30-21 | 1st Round Playoffs | | Fri., Nov. 15 | @ Fairview | L 20-41 | 2nd Round Playoffs |
| 2012 |
| Fri., Nov. 2 | vs. York Institute | W 35-7 | 1st Round Playoffs | | Fri., Nov. 9 | @ Christ Presbyterian | L 14-37 | 2nd Round Playoffs |
| 2008 |
| | Tyner Academy | W 21-20 | 1st Round Playoffs | | | Boyd-Buchanan | L 0-34 | 2nd Round Playoffs |
| 2007 |
| | Tyner Academy | L 13-26 | 1st Round Playoffs |
| 2006 |
| | Marion County | W 36-7 | 1st Round Playoffs | | | York Institute | W 31-28 | 2nd Round Playoffs | | | Smith County | L 21-26 | 3rd Round Playoffs |
| 2005 |
| | Marion County | L 20-21 | 1st Round Playoffs |
| 2003 |
| | Tyner Academy | L 0-40 | 1st Round Playoffs |
| 2002 |
| | Polk County | L 0-26 | 1st Round Playoffs |
| 2001 |
| | Polk County | L 6-14 | 1st Round Playoffs |
| 2000 |
| | Tyner Academy | W 28-21 | 1st Round Playoffs | | | Goodpasture | L 8-28 | 2nd Round Playoffs |
| 1999 |
| | Tyner Academy | L 12-38 | 1st Round Playoffs |
| 1998 |
| | Meigs County | W 27-26 | 1st Round Playoffs | | | Tyner Academy | L 12-24 | 2nd Round Playoffs |
| 1997 |
| | Marion County | W 30-14 | 1st Round Playoffs | | | David Lipscomb | L 16-24 | 2nd Round Playoffs |
| 1995 |
| | Tellico Plains | W 27-0 | 1st Round Playoffs | | | Webb | W 19-0 | 2nd Round Playoffs | | | Meigs County | L 14-21 | 3rd Round Playoffs |
| 1994 |
| | Notre Dame | W 42-21 | 1st Round Playoffs | | | Sweetwater | L 30-42 | 2nd Round Playoffs |
| 1993 |
| | Sweetwater | L 14-21 | 1st Round Playoffs |
| 1991 |
| | Loretto | L 14-21 | 1st Round Playoffs |
| 1989 |
| | Upperman | W 41-6 | 1st Round Playoffs | | | Ezell-Harding | W 29-7 | 2nd Round Playoffs | | | Oneida | L 7-10 | 3rd Round Playoffs |
| 1986 |
| | Celina | W 14-6 | 1st Round Playoffs | | | Nashville Christian | W 15-6 | 2nd Round Playoffs | | | Knoxville Catholic | W 28-6 | 3rd Round Playoffs | | | South Pittsburg | L 7-21 | Semi-finals Playoffs |
| 1980 |
| | Gordonsville | W 34-6 | 2nd Round Playoffs | | | Meigs County | L 13-28 | 3rd Round Playoffs |
| 1977 |
| | Cannon County | W 17-0 | 2nd Round Playoffs | | | Forrest | W 34-7 | 3rd Round Playoffs | | | Lake County | L 5-7 | Semi-finals Playoffs |
|
| Westmoreland Playoff Totals |
| Record |
21-28-0 892-1061 |
| Home Record | 3-0 |
| Away Record | 1-9 |
|
