| 2019 |
| Fri., Nov. 8 | @ South Doyle | L 3-41 | 1st Round Playoffs |
| 2016 |
| Fri., Nov. 4 | @ Knoxville Catholic | L 6-71 | 1st Round Playoffs |
| 2015 |
| Fri., Nov. 6 | @ Fulton | L 0-56 | 1st Round Playoffs |
| 2013 |
| Fri., Nov. 8 | @ Anderson County | L 28-54 | 1st Round Playoffs |
| 2012 |
| Sat., Nov. 3 | @ Morristown West | L 29-31 | 1st Round Playoffs |
| 2011 |
| Thu., Nov. 3 | @ Morristown East | L 0-43 | 1st Round Playoffs |
| 2008 |
| Fri., Nov. 7 | @ Sullivan South | L 14-49 | 1st Round Playoffs |
| 2005 |
| Fri., Nov. 4 | @ Tennessee | L 12-35 | 1st Round Playoffs |
| 2004 |
| Fri., Nov. 5 | vs. Elizabethton | L 8-28 | 1st Round Playoffs |
| 2003 |
| Fri., Nov. 7 | @ Elizabethton | W 25-13 | 1st Round Playoffs | | Fri., Nov. 14 | @ Greeneville | L 18-38 | 2nd Round Playoffs |
| 2001 |
| Fri., Nov. 2 | vs. Elizabethton | L 12-13 | 1st Round Playoffs |
| 1999 |
| | Daniel Boone | L 0-33 | 1st Round Playoffs |
| 1996 |
| | Knoxville Halls | L 0-16 | 1st Round Playoffs |
| 1994 |
| | Sullivan North | W 14-12 | 1st Round Playoffs | | | Shelbyville | W 21-7 | 2nd Round Playoffs | | | Powell | W 24-21 | 3rd Round Playoffs | | | Cleveland | L 6-38 | Semi-finals Playoffs |
| 1989 |
| | Dobyns-Bennett | L 0-21 | 1st Round Playoffs |
| 1988 |
| | Science Hill | W 21-14 | 1st Round Playoffs | | | Oak Ridge | L 0-21 | 2nd Round Playoffs |
|
| Cherokee Playoff Totals |
| Record |
5-16-0 241-655 |
| Home Record | 0-2 |
| Away Record | 1-9 |
|
