| 2020 |
| Fri., Nov. 6 | @ Goodpasture | L 21-28 | 1st Round Playoffs |
| 2019 |
| Fri., Nov. 8 | @ CPA | L 0-35 | 1st Round Playoffs |
| 2018 |
| Sat., Nov. 3 | vs. Chattanooga Christian | W 48-27 | 1st Round Playoffs | | Sat., Nov. 10 | vs. BGA | L 10-30 | 2nd Round Playoffs |
| 2017 |
| Fri., Nov. 3 | vs. Chattanooga Christian | W 42-21 | 1st Round Playoffs | | Fri., Nov. 10 | @ CPA | L 7-42 | 2nd Round Playoffs |
| 2016 |
| Fri., Nov. 4 | vs. Ezell-Harding | W 49-13 | 2nd Round Playoffs | | Fri., Nov. 11 | vs. Harding Academy | W 24-21 | 3rd Round Playoffs | | Fri., Nov. 18 | @ St. Georges | W 69-48 | Semi-finals Playoffs | | Thu., Dec. 1 | Lausanne | L 9-12 | Championship Game @ Cookeville |
| 2015 |
| Fri., Nov. 6 | @ University School of Jackson | L 6-7 | 1st Round Playoffs |
| 2014 |
| Fri., Nov. 14 | vs. Davidson Academy | W 62-20 | 3rd Round Playoffs | | Fri., Nov. 21 | vs. Evangelical Christian | W 21-7 | Semi-finals Playoffs | | Thu., Dec. 4 | BGA | W 38-21 | Championship Game @ Cookeville |
| 2013 |
| Fri., Nov. 15 | vs. University School of Jackson | W 48-21 | 3rd Round Playoffs | | Fri., Nov. 22 | @ Evangelical Christian | W 28-15 | Semi-finals Playoffs | | Thu., Dec. 5 | St. Georges | W 28-14 | Championship Game @ Cookeville |
| 2012 |
| Fri., Nov. 9 | vs. Harding Academy | W 49-21 | 3rd Round Playoffs | | Fri., Nov. 16 | vs. DCA | W 44-0 | Semi-finals Playoffs | | Thu., Nov. 29 | Evangelical Christian | W 47-14 | Championship Game @ Cookeville |
| 2011 |
| | SBEC (MS) | W 49-0 | 3rd Round Playoffs | | | USJ | L 27-48 | Semi-finals Playoffs |
| 2010 |
| | USJ | W 41-14 | 3rd Round Playoffs | | | ECS | W 28-23 | Semi-finals Playoffs | | | St. Georges | W 42-7 | Championship Game |
| 2009 |
| | ECS | W 42-28 | Semi-finals Playoffs | | | USJ | W 30-0 | Championship Game |
| 2007 |
| | MBA | L 14-49 | 3rd Round Playoffs |
| 2006 |
| | Pope John Paul II | W 34-33 | Semi-finals Playoffs | | | ECS | W 17-14 | Championship Game |
| 2005 |
| | Pope John Paul II | W 28-7 | Semi-finals Playoffs | | | ECS | L 0-26 | Championship Game |
| 2004 |
| | Pope John Paul II | W 42-21 | 3rd Round Playoffs | | | ECS | L 22-24 | Semi-finals Playoffs |
| 2003 |
| | BGA | L 7-23 | 3rd Round Playoffs |
| 2002 |
| | BGA | L 0-21 | 3rd Round Playoffs |
| 2001 |
| | Notre Dame | W 45-24 | 3rd Round Playoffs | | | Briarcrest | L 19-47 | Semi-finals Playoffs |
| 2000 |
| | Harding Academy | L 7-17 | 3rd Round Playoffs |
| 1999 |
| | Fayette Academy | W 35-15 | 3rd Round Playoffs | | | Briarcrest | L 13-35 | Semi-finals Playoffs |
| 1998 |
| | Goodpasture | W 46-33 | 3rd Round Playoffs | | | Briarcrest | L 7-30 | Semi-finals Playoffs |
| 1997 |
| | Notre Dame | W 14-0 | 1st Round Playoffs | | | Briarcrest | W 35-6 | 2nd Round Playoffs | | | BGA | L 7-19 | 3rd Round Playoffs |
| 1996 |
| | Powell Valley | W 41-15 | 1st Round Playoffs | | | Smith County | W 29-7 | 2nd Round Playoffs | | | Hampton | W 28-19 | 3rd Round Playoffs | | | Upperman | W 28-13 | Semi-finals Playoffs | | | Goodpasture | W 27-20 | Championship Game |
| 1995 |
| | Powell Valley | W 48-0 | 1st Round Playoffs | | | Westmoreland | L 0-19 | 2nd Round Playoffs |
| 1992 |
| | South Doyle | L 9-15 | 1st Round Playoffs |
| 1990 |
| | Chattanooga | W 41-0 | 1st Round Playoffs | | | Oneida | W 33-0 | 2nd Round Playoffs | | | FRA | L 24-28 | 3rd Round Playoffs |
| 1989 |
| | Cooper Basin | W 14-13 | 1st Round Playoffs | | | Coalfield | L 20-22 | 2nd Round Playoffs |
| 1988 |
| | Johnson County | L 17-21 | 1st Round Playoffs |
| 1987 |
| | South Greene | L 20-21 | 1st Round Playoffs |
| 1984 |
| | Gatlinburg-Pittman | W 28-3 | 2nd Round Playoffs | | | Cooper Basin | L 14-28 | 3rd Round Playoffs |
| 1981 |
| | Sweetwater | W 13-10 | 2nd Round Playoffs | | | Coalfield | W 20-16 | 3rd Round Playoffs | | | Meigs County | W 32-2 | Semi-finals Playoffs | | | Memphis Prep | W 7-6 | Championship Game |
| 1979 |
| | Alcoa | L 0-22 | 2nd Round Playoffs |
| 1978 |
| | Alcoa | L 0-47 | 2nd Round Playoffs |
|
| Webb Playoff Totals |
| Record |
43-26-0 1794-1328 |
| Home Record | 9-1 |
| Away Record | 2-4 |
|
