| 2023 |
| Fri., Oct. 27 | vs. Oak Hill Academy | W 57-20 | 1st Round Playoffs | | Fri., Nov. 3 | @ Washington Academy | W 35-7 | 2nd Round Playoffs | | Fri., Nov. 10 | @ Bowling Green LA | L 13-42 | Semi-finals Playoffs |
| 2022 |
| Fri., Oct. 28 | vs. Marshall Academy | W 36-0 | 1st Round Playoffs | | Fri., Nov. 4 | @ Adams Christian | L 14-15 | 2nd Round Playoffs |
| 2021 |
| Fri., Oct. 29 | vs. Riverfield Academy LA | L 8-28 | 1st Round Playoffs |
| 2020 |
| Fri., Oct. 30 | Bye | - | 1st Round Playoffs | | Fri., Nov. 6 | vs. Cathedral | W 18-0 | 2nd Round Playoffs | | Fri., Nov. 13 | @ Riverfield Academy LA | L 22-49 | Semi-finals Playoffs |
| 2019 |
| Fri., Nov. 1 | @ Cathedral | L 18-44 | 1st Round Playoffs |
| 2011 |
| Fri., Nov. 4 | @ River Oaks LA | L 21-50 | 1st Round Playoffs |
| 2010 |
| Fri., Nov. 5 | vs. Indianola Academy | W 32-7 | 1st Round Playoffs | | Fri., Nov. 12 | vs. Leake Academy | L 21-23 | 2nd Round Playoffs |
| 2009 |
| Fri., Nov. 6 | vs. Indianola Academy | L 19-21 | 1st Round Playoffs |
| 2008 |
| Fri., Nov. 7 | vs. Copiah Academy | W 32-18 | 1st Round Playoffs | | Fri., Nov. 14 | vs. Lee Academy | L 7-14 | 2nd Round Playoffs |
| 2007 |
| Fri., Nov. 9 | @ Lee Academy | W 13-7 | 1st Round Playoffs | | Fri., Nov. 16 | vs. Indianola Academy | W 28-21 | 2nd Round Playoffs | | Fri., Nov. 23 | @ Marshall Academy | L 7-14 | Semi-finals Playoffs |
| 2006 |
| Fri., Nov. 10 | vs. Indianola Academy | W 35-0 | 1st Round Playoffs | | Thu., Nov. 16 | vs. Central Hinds Academy | W 25-0 | 2nd Round Playoffs | | Fri., Nov. 24 | vs. Kirk Academy | L 6-37 | Semi-finals Playoffs |
| 2005 |
| Fri., Nov. 11 | @ Lee Academy | L 16-40 | 1st Round Playoffs |
| 2001 |
| Fri., Nov. 16 | vs. Marshall Academy | L 26-27 (OT) | 1st Round Playoffs |
| 2000 |
| Fri., Nov. 3 | @ Marvell Academy AR | W 49-42 | 1st Round Playoffs | | Fri., Nov. 10 | @ Kirk Academy | W 56-21 | Semi-finals Playoffs | | Fri., Nov. 17 | Bowling Green LA | W 29-12 | Championship Game |
| 1999 |
| Fri., Nov. 5 | vs. Bowling Green LA | W 40-14 | 1st Round Playoffs | | Fri., Nov. 12 | vs. Prentiss Christian | W 44-22 | Semi-finals Playoffs | | Fri., Nov. 19 | Magnolia Heights | W 34-13 | Championship Game |
| 1998 |
| Fri., Nov. 6 | vs. Brookhaven Academy | W 36-13 | 1st Round Playoffs | | Fri., Nov. 13 | vs. Bowling Green LA | W 38-24 | Semi-finals Playoffs | | Fri., Nov. 20 | Magnolia Heights | W 63-42 | Championship Game |
| 1997 |
| Fri., Nov. 7 | vs. Central Academy | W 42-14 | 1st Round Playoffs | | Fri., Nov. 14 | vs. North Sunflower Academy | W 27-18 | 2nd Round Playoffs | | Fri., Nov. 21 | vs. Wayne Academy | W 21-14 | Semi-finals Playoffs | | Fri., Nov. 28 | Tri-County Academy | W 41-20 | Championship Game |
| 1996 |
| Fri., Nov. 8 | vs. Strider Academy | W 25-20 | 1st Round Playoffs | | Fri., Nov. 15 | vs. West Memphis AR | L 13-49 | 2nd Round Playoffs |
| 1993 |
| Fri., Nov. 5 | @ Central Hinds Academy | L 8-43 | 1st Round Playoffs |
| 1991 |
| Fri., Nov. 8 | @ Prentiss Christian | W 23-0 | 1st Round Playoffs | | Fri., Nov. 15 | vs. Tri-County Academy | W 31-0 | Semi-finals Playoffs | | Fri., Nov. 22 | Tunica Academy | L 13-23 | Championship Game |
| 1987 |
| Fri., Nov. 13 | vs. Prentiss Christian | L 8-29 | Semi-finals Playoffs |
| 1986 |
| Fri., Nov. 14 | @ Sharkey-Issaquena Academy | W 22-16 | Semi-finals Playoffs | | Fri., Nov. 21 | vs. Marvell Academy AR | L 14-16 | Championship Game |
| 1983 |
| Fri., Nov. 11 | vs. Trinity Episcopal | W 28-22 | Semi-finals Playoffs | | Fri., Nov. 18 | @ Cruger-Tchula Academy | W 32-7 | Championship Game |
| 1975 |
| Fri., Nov. 7 | vs. Strider Academy | W 7-0 | 1st Round Playoffs | | Fri., Nov. 14 | @ Magnolia Heights | W 12-7 | Semi-finals Playoffs | | Fri., Nov. 21 | vs. Trinity Episcopal | W 33-16 | Championship Game |
| 1974 |
| Fri., Nov. 8 | Strider Academy | L 6-18 | 1st Round Playoffs |
|
| Winston Academy Playoff Totals |
| Record |
32-19-0 1304-1019 |
| Home Record | 20-9 |
| Away Record | 8-8 |
|
