| Tue 9/03 | Boys Soccer | Shady Side Academy @ Valley (Valley - Memorial Stadium) | Final | 9 - 1 |
| Thu 9/05 | Boys Soccer | Leechburg @ Shady Side Academy | Final | 0 - 5 |
| Tue 9/10 | Boys Soccer | Shady Side Academy @ Derry (Derry Area - Trojan Field) | Final | 7 - 1 |
| Thu 9/12 | Boys Soccer | Shady Side Academy @ Burrell (Burrell - Buccaneer Stadium) | Final | 5 - 0 |
| Sat 9/14 | Boys Soccer | Freeport @ Shady Side Academy (Shady Side Academy) | Final | 0 - 1 |
| Tue 9/17 | Boys Soccer | Shady Side Academy @ Mt. Pleasant (Mount Pleasant- Viking Stadium) | Final | 3 - 0 |
| Thu 9/19 | Boys Soccer | Deer Lakes @ Shady Side Academy | Final | 0 - 1 |
| Sat 9/21 | Boys Soccer | Valley @ Shady Side Academy (Shady Side Academy) | Final | 0 - 8 |
| Tue 9/24 | Boys Soccer | Shady Side Academy @ Leechburg | Final | 9 - 0 |
| Thu 9/26 | Boys Soccer | Derry @ Shady Side Academy (Shady Side Academy) | Final | 0 - 9 |
| Tue 10/01 | Boys Soccer | Burrell @ Shady Side Academy (Shady Side Academy) | Final | 3 - 2 |
| Thu 10/03 | Boys Soccer | Shady Side Academy @ Freeport (Freeport - James E. Swartz Stadium) | Final | 0 - 0 |
| Mon 10/07 | Boys Soccer | Mt. Pleasant @ Shady Side Academy | Final | 0 - 2 |
| Thu 10/10 | Boys Soccer | Shady Side Academy @ Deer Lakes | Final | 0 - 1 |
| Tue 10/15 | Boys Soccer | North Hills @ Shady Side Academy (Shady Side Academy) | Final | 0 - 2 |
| Sat 10/19 | Boys Soccer | Shady Side Academy @ Waynesburg (Upper St. Clair) | Final | 4 - 0 |
| Wed 10/23 | Boys Soccer | Charleroi @ Shady Side Academy (Plum - Mustang Stadium) | Final | 0 - 1 |
| Sat 10/26 | Boys Soccer | Shady Side Academy @ Quaker Valley (North Allegheny - Newman Stadium) | Final | 0 - 2 |
| Wed 10/30 | Boys Soccer | South Park @ Shady Side Academy (Mars - Planet Stadium) | Final | 1 - 3 |
| Tue 11/05 | Boys Soccer | Shady Side Academy @ Mercyhurst Prep (Erie, Pennsylvania) | Final | 1 - 2 |
