| Fri 8/30 | Football | Shady Side Academy @ Brownsville (Brownsville - Redstone Field) | Final | 35 - 12 |
| Fri 9/06 | Football | Valley @ Shady Side Academy (Shady Side Academy) | Final | 0 - 27 |
| Fri 9/13 | Football | Steel Valley @ Shady Side Academy (Shady Side Academy) | Final | 6 - 29 |
| Fri 9/20 | Football | Shady Side Academy @ Neshannock (Neshannock High School) | Final | 14 - 54 |
| Fri 9/27 | Football | Shady Side Academy @ Apollo-Ridge (Apollo-Ridge High School) | Final | 0 - 10 |
| Fri 10/04 | Football | Summit Academy @ Shady Side Academy (Shady Side Academy) | Final | 20 - 28 |
| Sat 10/12 | Football | Fort Cherry @ Shady Side Academy (Shady Side Academy) | Final | 6 - 21 |
| Fri 10/18 | Football | Shady Side Academy @ East Allegheny (East Allegheny High School) | Final | 27 - 42 |
| Fri 10/25 | Football | Avonworth @ Shady Side Academy (Shady Side Academy) | Final | 35 - 7 |
| Fri 11/01 | Football | Shady Side Academy @ Washington (Washington High School Stadium) | Final | 7 - 21 |
