| 2020 |
| Fri., Nov. 6 | @ Red Bank | L 6-50 | 1st Round Playoffs |
| 2014 |
| Fri., Nov. 7 | @ McMinn Central | L 14-43 | 1st Round Playoffs |
| 2013 |
| Fri., Nov. 8 | @ Upperman | L 20-42 | 1st Round Playoffs |
| 2012 |
| Fri., Nov. 2 | @ Cheatham County | L 30-69 | 1st Round Playoffs |
| 2011 |
| | Goodpasture | L 6-42 | 1st Round Playoffs |
| 2009 |
| | Goodpasture | L 27-38 | 1st Round Playoffs |
| 2004 |
| | Portland | L 6-48 | 1st Round Playoffs |
| 2003 |
| | Trousdale County | W 16-15 | 1st Round Playoffs | | | Macon County | L 15-17 | 2nd Round Playoffs |
| 2002 |
| | Livingston Academy | W 35-14 | 1st Round Playoffs | | | Trousdale County | L 10-29 | 2nd Round Playoffs |
| 2001 |
| | Smith County | L 7-33 | 1st Round Playoffs |
| 2000 |
| | Greenbrier | W 26-19 | 1st Round Playoffs | | | Portland | L 7-61 | 2nd Round Playoffs |
| 1999 |
| | Portland | L 7-51 | 1st Round Playoffs |
| 1995 |
| | Kingston | L 11-30 | 1st Round Playoffs |
| 1994 |
| | Loudon | L 0-24 | 1st Round Playoffs |
| 1993 |
| | Scott | W 24-14 | 1st Round Playoffs | | | Knoxville West | W 38-7 | 2nd Round Playoffs | | | McMinn Central | L 7-17 | 3rd Round Playoffs |
| 1991 |
| | Sweetwater | L 14-28 | 1st Round Playoffs |
|
| Grundy County Playoff Totals |
| Record |
5-16-0 326-691 |
| Home Record | 0-0 |
| Away Record | 0-4 |
|
