| Date | H/A | W/L | Team | Score | Opponent | Score | |
| 2008-08-29 | H | W | Oliver (PA) | 40 | Langley (PA) (4) | 2 | 1719 |
| 2008-09-05 | H | L | Oliver (PA) | 6 | Westinghouse (PA) (1) | 24 | 1727 |
| 2008-09-12 | A | W | Oliver (PA) | 20 | Allderdice (PA) (0) | 0 | 1728 |
| 2008-09-19 | A | L | Oliver (PA) | 20 | Schenley (PA) (3) | 22 | 1729 |
| 2008-09-26 | H | L | Oliver (PA) | 0 | Perry Traditional Acad. (PA) (2) | 6 | 1730 |
| 2008-10-03 | A | L | Oliver (PA) | 13 | Wheeling Central (8) | 34 | 1289 |
| 2008-10-11 | A | L | Oliver (PA) | 12 | Carrick (PA) (1) | 18 | 1731 |
| 2008-10-18 | H | L | Oliver (PA) | 14 | Brashear (PA) (5) | 33 | 1732 |
| 2008-10-24 | A | L | Oliver (PA) | 18 | Peabody (PA) (1) | 38 | 1733 |