| 2023 |
| Fri., Nov. 3 | vs. South Delta | L 12-20 | 1st Round Playoffs |
| 2010 |
| Fri., Nov. 12 | vs. French Camp Academy | W 41-13 | 1st Round Playoffs | | Fri., Nov. 19 | @ Nanih Waiya | W 34-14 | 2nd Round Playoffs | | Fri., Nov. 26 | vs. Dexter | W 19-7 | Semi-finals Playoffs | | Fri., Dec. 3 | Durant | W 20-14 | Championship Game |
| 2009 |
| Fri., Nov. 13 | vs. French Camp Academy | W 33-6 | 1st Round Playoffs | | Fri., Nov. 20 | @ Nanih Waiya | W 10-7 | 2nd Round Playoffs | | Fri., Nov. 27 | vs. Sebastopol | W 15-7 | Semi-finals Playoffs | | Thu., Dec. 3 | Durant | W 27-26 | Championship Game |
| 2008 |
| Fri., Nov. 14 | vs. Sebastopol | W 28-8 | 1st Round Playoffs | | Fri., Nov. 21 | @ Durant | W 33-6 | 2nd Round Playoffs | | Fri., Nov. 28 | @ Puckett | L 12-28 | Semi-finals Playoffs |
| 2007 |
| Fri., Nov. 16 | vs. Nanih Waiya | W 47-14 | 1st Round Playoffs | | Fri., Nov. 23 | @ Weir | L 12-28 | 2nd Round Playoffs |
| 2006 |
| Fri., Nov. 10 | vs. Nanih Waiya | W 46-14 | 1st Round Playoffs | | Fri., Nov. 17 | vs. Lake | L 22-26 | 2nd Round Playoffs |
| 2005 |
| Fri., Nov. 18 | vs. Nanih Waiya | W 41-7 | 1st Round Playoffs | | Fri., Nov. 25 | vs. Lake | W 41-9 | 2nd Round Playoffs | | Fri., Dec. 2 | @ Saint John | W 28-7 | Semi-finals Playoffs | | Sat., Dec. 10 | Brooks | L 33-52 | Championship Game |
| 2004 |
| Fri., Nov. 12 | vs. Noxapater | W 46-8 | 1st Round Playoffs | | Fri., Nov. 19 | @ Scott Central | L 22-35 | 2nd Round Playoffs |
| 2003 |
| Fri., Nov. 14 | @ Puckett | L 7-56 | 1st Round Playoffs |
| 1997 |
| Fri., Nov. 14 | @ Pelahatchie | L 8-20 | 1st Round Playoffs |
| 1996 |
| Fri., Nov. 15 | @ Cathedral | W 11-0 | 1st Round Playoffs | | Fri., Nov. 22 | vs. Saint Aloysius | W 36-14 | 2nd Round Playoffs | | Fri., Nov. 29 | vs. Mize | W 21-0 | Semi-finals Playoffs | | Fri., Dec. 6 | Weir | L 6-33 | Championship Game |
| 1995 |
| Fri., Nov. 10 | vs. Sebastopol | W 30-6 | 1st Round Playoffs | | Fri., Nov. 17 | @ Salem | L 20-25 | 2nd Round Playoffs |
| 1993 |
| Fri., Nov. 12 | @ Cathedral | L 14-28 | 1st Round Playoffs |
| 1992 |
| Fri., Nov. 13 | @ Scott Central | W 19-0 | 1st Round Playoffs | | Fri., Nov. 20 | vs. Utica | W 24-6 | 2nd Round Playoffs | | Fri., Nov. 27 | @ Stringer | L 7-25 | Semi-finals Playoffs |
| 1991 |
| Fri., Nov. 15 | @ Anguilla | W 26-22 | 1st Round Playoffs | | Fri., Nov. 22 | vs. Scott Central | L 12-30 | 2nd Round Playoffs |
| 1990 |
| Fri., Nov. 9 | vs. Enterprise Clarke | W 32-13 | 1st Round Playoffs | | Fri., Nov. 16 | vs. Mize | L 6-19 | 2nd Round Playoffs |
| 1989 |
| Fri., Nov. 10 | vs. Mize | W 27-13 | 1st Round Playoffs | | Fri., Nov. 17 | @ Noxapater | W 56-7 | 2nd Round Playoffs | | Fri., Nov. 24 | vs. Enterprise Clarke | W 22-6 | Semi-finals Playoffs | | | Smithville | W 19-16 | Championship Game |
| 1988 |
| Fri., Nov. 11 | @ Sumrall | L 26-27 | 1st Round Playoffs |
| 1987 |
| Fri., Nov. 13 | vs. Lake | L 7-17 | 1st Round Playoffs |
| 1985 |
| | vs. Cathedral | W 33-8 | 1st Round Playoffs | | | @ McLain | W 26-3 | Semi-finals Playoffs | | | Weir | L 0-21 | Championship Game |
| 1984 |
| Fri., Nov. 23 | vs. Utica | L 6-15 | 1st Round Playoffs |
| 1981 |
| | Saint Aloysius | L 10-24 | 1st Round Playoffs |
| 1949 |
| Fri., Nov. 25 | Perkinston | L 0-39 | 1st Round Playoffs |
| 1948 |
| Fri., Dec. 3 | Flora | L 0-26 | 1st Round Playoffs |
|
| Mount Olive Playoff Totals |
| Record |
30-21-0 1133-875 |
| Home Record | 18-6 |
| Away Record | 9-9 |
|
