| 2020 |
| Fri., Nov. 6 | vs. Midway | W 38-33 | 1st Round Playoffs | | Fri., Nov. 13 | vs. Oliver Springs | L 20-24 | 2nd Round Playoffs |
| 2019 |
| Fri., Nov. 8 | vs. Harriman | W 28-7 | 1st Round Playoffs | | Fri., Nov. 15 | vs. Oliver Springs | L 0-29 | 2nd Round Playoffs |
| 2018 |
| Sat., Nov. 3 | vs. Midway | W 36-22 | 1st Round Playoffs | | Sat., Nov. 10 | vs. Coalfield | L 24-29 | 2nd Round Playoffs |
| 2017 |
| Fri., Nov. 3 | vs. Midway | W 50-13 | 1st Round Playoffs | | Fri., Nov. 10 | vs. Coalfield | L 8-48 | 2nd Round Playoffs |
| 2016 |
| Fri., Nov. 4 | vs. Harriman | W 60-56 | 1st Round Playoffs | | Fri., Nov. 11 | vs. Coalfield | L 14-54 | 2nd Round Playoffs |
| 2015 |
| Fri., Nov. 6 | vs. Coalfield | L 6-38 | 1st Round Playoffs |
| 2014 |
| Fri., Nov. 14 | vs. Coalfield | L 28-38 | 2nd Round Playoffs |
| 2013 |
| Fri., Nov. 8 | vs. Midway | L 14-26 | 1st Round Playoffs |
| 2012 |
| Sat., Nov. 3 | vs. Midway | W 28-12 | 1st Round Playoffs | | Sat., Nov. 10 | @ Coalfield | L 14-38 | 2nd Round Playoffs |
| 2010 |
| | Greenback | L 8-30 | 1st Round Playoffs |
| 2009 |
| | Sunbright | L 38-54 | 1st Round Playoffs |
| 2008 |
| | Oneida | L 18-41 | 1st Round Playoffs |
| 2007 |
| | Harriman | L 7-18 | 1st Round Playoffs |
| 2005 |
| | Midway | W 20-13 | 1st Round Playoffs | | | Coalfield | L 6-13 | 2nd Round Playoffs |
| 2004 |
| | Oneida | L 0-23 | 1st Round Playoffs |
| 2003 |
| | CAK | L 30-31 | 1st Round Playoffs |
| 2002 |
| | Midway | W 48-6 | 1st Round Playoffs | | | Powell Valley | W 46-6 | 2nd Round Playoffs | | | Greenback | W 22-7 | 3rd Round Playoffs | | | Boyd-Buchanan | L 8-39 | Semi-finals Playoffs |
| 2001 |
| | Coalfield | W 30-0 | 1st Round Playoffs | | | Greenback | W 60-21 | 2nd Round Playoffs | | | Midway | W 44-15 | 3rd Round Playoffs | | | South Pittsburg | W 44-6 | Semi-finals Playoffs | | | Ezell-Harding | L 26-63 | Championship Game |
| 2000 |
| | Oliver Springs | W 24-20 | 1st Round Playoffs | | | Austin-East | L 8-26 | 2nd Round Playoffs |
| 1999 |
| | Harriman | L 14-28 | 1st Round Playoffs |
| 1998 |
| | Boyd-Buchanan | L 22-38 | 1st Round Playoffs |
| 1996 |
| | Greenback | W 42-0 | 1st Round Playoffs | | | CPA | W 20-0 | 2nd Round Playoffs | | | BGA | L 6-35 | 3rd Round Playoffs |
| 1995 |
| | Copper Basin | W 34-0 | 1st Round Playoffs | | | Trousdale County | L 12-14 | 2nd Round Playoffs |
| 1994 |
| | Greenback | L 6-21 | 1st Round Playoffs |
| 1993 |
| | Gordonsville | L 8-22 | 1st Round Playoffs |
| 1992 |
| | Coalfield | W 14-8 | 1st Round Playoffs | | | Greenback | L 6-28 | 2nd Round Playoffs |
| 1991 |
| Fri., Nov. 15 | vs. Oneida | L 6-28 | 1st Round Playoffs |
| 1990 |
| | Oneida | L 0-15 | 1st Round Playoffs |
| 1989 |
| | Oneida | L 0-24 | 1st Round Playoffs |
| 1988 |
| | Oneida | W 7-3 | 1st Round Playoffs | | | Midway | L 7-40 | 2nd Round Playoffs |
| 1987 |
| | Oneida | W 14-12 | 1st Round Playoffs | | | South Pittsburg | L 0-28 | 2nd Round Playoffs |
| 1986 |
| | Knoxville Catholic | L 6-21 | 1st Round Playoffs |
| 1985 |
| | Knoxville Catholic | L 6-14 | 1st Round Playoffs |
|
| Cloudland Playoff Totals |
| Record |
21-33-0 1085-1278 |
| Home Record | 6-9 |
| Away Record | 0-1 |
|
