| 2023 |
| Fri., Oct. 27 | @ Oak Forest Academy LA | L 23-55 | 1st Round Playoffs |
| 2022 |
| Fri., Oct. 28 | vs. Silliman LA | W 31-28 | 1st Round Playoffs | | Fri., Nov. 4 | @ Heritage Academy | L 24-48 | 2nd Round Playoffs |
| 2021 |
| Fri., Oct. 29 | @ Central Hinds Academy | W 34-30 | 1st Round Playoffs | | Fri., Nov. 5 | @ Leake Academy | L 14-49 | 2nd Round Playoffs |
| 2020 |
| Fri., Oct. 30 | vs. Saint Aloysius | W 62-28 | 1st Round Playoffs | | Fri., Nov. 6 | @ Adams Christian | L 19-30 | 2nd Round Playoffs |
| 2019 |
| Fri., Nov. 8 | vs. Hartfield Academy | W 46-31 | 2nd Round Playoffs | | Fri., Nov. 15 | @ Heritage Academy | L 14-47 | Semi-finals Playoffs |
| 2018 |
| Fri., Nov. 2 | @ Washington Academy | W 34-7 | 1st Round Playoffs | | Fri., Nov. 9 | @ Lamar | L 36-41 | Semi-finals Playoffs |
| 2017 |
| Fri., Nov. 10 | vs. Simpson Academy | L 15-36 | Semi-finals Playoffs |
| 2016 |
| Fri., Nov. 4 | vs. East Rankin Academy | W 47-26 | 1st Round Playoffs | | Fri., Nov. 11 | @ Lamar | L 34-55 | Semi-finals Playoffs |
| 2015 |
| Fri., Nov. 6 | vs. East Rankin Academy | L 13-14 | 1st Round Playoffs |
| 2010 |
| Fri., Nov. 5 | vs. East Rankin Academy | W 28-17 | 1st Round Playoffs | | Thu., Nov. 11 | Oak Forest Academy LA | W 28-14 | Championship Game |
| 2009 |
| Fri., Nov. 6 | @ East Rankin Academy | W 27-14 | 1st Round Playoffs | | Thu., Nov. 12 | Washington Academy | L 7-34 | Championship Game |
| 2008 |
| Fri., Nov. 7 | vs. Madison-Ridgeland Academy | L 23-28 | 1st Round Playoffs |
| 2007 |
| Fri., Nov. 9 | @ Jackson Prep | L 0-38 | 1st Round Playoffs |
| 2006 |
| Fri., Nov. 10 | vs. Madison-Ridgeland Academy | L 10-22 | 1st Round Playoffs |
| 2004 |
| Fri., Nov. 12 | @ Jackson Prep | L 14-31 | 1st Round Playoffs |
| 2003 |
| Fri., Nov. 14 | @ Jackson Prep | L 7-35 | 1st Round Playoffs |
| 2000 |
| Fri., Nov. 10 | Jackson Academy | W 19-0 | 1st Round Playoffs | | Fri., Nov. 17 | Jackson Prep | L 21-30 | Championship Game |
| 1999 |
| Fri., Nov. 12 | Jackson Academy | W 35-23 | 1st Round Playoffs | | Fri., Nov. 19 | Jackson Prep | W 34-13 | Championship Game |
| 1997 |
| Fri., Nov. 14 | Jackson Prep | W 24-14 | 1st Round Playoffs | | Fri., Nov. 21 | Madison-Ridgeland Academy | W 38-16 | Championship Game |
| 1996 |
| Fri., Nov. 15 | Jackson Prep | L 7-31 | Semi-finals Playoffs |
| 1995 |
| Fri., Nov. 10 | Carroll Academy | L 3-14 | 1st Round Playoffs |
| 1993 |
| Fri., Nov. 12 | vs. Jackson Prep | W 21-7 | 1st Round Playoffs | | Fri., Nov. 26 | Parklane Academy | L 3-35 | Championship Game |
| 1992 |
| Fri., Nov. 13 | @ Madison-Ridgeland Academy | L 0-32 | 1st Round Playoffs |
| 1991 |
| Fri., Nov. 15 | @ Jackson Prep | L 14-35 | 1st Round Playoffs |
| 1990 |
| Fri., Nov. 9 | @ Jackson Prep | L 0-12 | 1st Round Playoffs |
|
| Pillow Academy Playoff Totals |
| Record |
15-22-0 809-1020 |
| Home Record | 6-4 |
| Away Record | 3-13 |
|
