| 2019 |
| Fri., Nov. 8 | @ Hardin County | L 14-42 | 1st Round Playoffs |
| 2018 |
| Fri., Nov. 2 | @ Jackson North Side | L 6-50 | 1st Round Playoffs |
| 2015 |
| Fri., Nov. 6 | @ Kenwood | L 20-26 | 1st Round Playoffs |
| 2012 |
| Fri., Nov. 2 | @ Centennial | L 10-44 | 1st Round Playoffs |
| 2005 |
| | Hillsboro | L 0-42 | 1st Round Playoffs |
| 2004 |
| | Grundy County | W 48-6 | 1st Round Playoffs | | | Smith County | L 7-12 | 2nd Round Playoffs |
| 2003 |
| | Walker Valley | W 37-12 | 1st Round Playoffs | | | Smith County | L 20-34 | 2nd Round Playoffs |
| 2002 |
| | Howard | W 19-16 | 1st Round Playoffs | | | Smith County | L 13-14 | 2nd Round Playoffs |
| 2001 |
| | Sequoyah | W 65-0 | 1st Round Playoffs | | | Howard | W 50-0 | 2nd Round Playoffs | | | Trousdale County | L 14-17 | 3rd Round Playoffs |
| 2000 |
| | Howard | W 58-0 | 1st Round Playoffs | | | Grundy County | W 61-7 | 2nd Round Playoffs | | | White House | W 19-10 | 3rd Round Playoffs | | | Seymour | W 45-13 | Semi-finals Playoffs | | | Covington | W 43-0 | Championship Game |
| 1999 |
| | Grundy County | W 51-7 | 1st Round Playoffs | | | Brainerd | W 34-20 | 2nd Round Playoffs | | | Sequoyah | W 46-28 | 3rd Round Playoffs | | | Seymour | W 21-0 | Semi-finals Playoffs | | | Milan | L 14-21 | Championship Game |
| 1998 |
| | Brainerd | W 44-14 | 1st Round Playoffs | | | Livingston Academy | W 34-15 | 2nd Round Playoffs | | | White House | L 14-21 | 3rd Round Playoffs |
| 1997 |
| | Chattanooga Central | W 34-24 | 1st Round Playoffs | | | White House | L 13-21 | 2nd Round Playoffs |
| 1996 |
| | Hickman County | W 21-0 | 1st Round Playoffs | | | Melrose | L 32-54 | 2nd Round Playoffs |
| 1995 |
| | Waverly Central | W 42-7 | 1st Round Playoffs | | | Raleigh Egypt | W 22-0 | 2nd Round Playoffs | | | Milan | W 13-0 | 3rd Round Playoffs | | | Humboldt | L 20-21 | Semi-finals Playoffs |
| 1994 |
| | Page | W 55-14 | 1st Round Playoffs | | | Union City | W 47-21 | 2nd Round Playoffs | | | Waverly Central | W 23-0 | 3rd Round Playoffs | | | Springfield | W 30-14 | Semi-finals Playoffs | | | Marion County | L 14-43 | Championship Game |
| 1993 |
| | Waverly Central | L 7-14 | 1st Round Playoffs |
| 1990 |
| | Lewis County | W 21-7 | 1st Round Playoffs | | | Brentwood Academy | L 7-47 | 2nd Round Playoffs |
| 1987 |
| | Hickman County | L 0-9 | 1st Round Playoffs |
| 1986 |
| | Marshall County | L 0-40 | 1st Round Playoffs |
| 1983 |
| | Marshall County | W 10-7 | 2nd Round Playoffs | | | Brentwood Academy | L 14-41 | 3rd Round Playoffs |
| 1980 |
| | York Institute | W 27-0 | 2nd Round Playoffs | | | Kingston | L 15-20 | 3rd Round Playoffs |
| 1979 |
| | York Institute | L 13-18 | 2nd Round Playoffs |
|
| Portland Playoff Totals |
| Record |
28-22-0 1287-893 |
| Home Record | 0-0 |
| Away Record | 0-4 |
|
