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Team schedule for 2008-2009 Oliver football
Conference record: 2-6-0 Overall: 2-8-0
City League - Class AAAA & AAA
* Conference games | PPD Postponed | F Forfeit
| Date | Opponent | Venue | Score |
|---|---|---|---|
| 8/29 3:30 pm | Langley * | Cupples Stadium | W 40-2 |
| 9/5 3:30 pm | Westinghouse * | Cupples Stadium | L 24-6 |
| 9/12 3:30 pm | at Allderdice * | Cupples Stadium | W 20-0 |
| 9/19 3:30 pm | at Schenley * | Cupples Stadium | L 22-20 |
| 9/26 7:30 pm | Perry Traditional Academy * | Cupples Stadium | L 6-0 |
| 10/3 7 pm | at Wheeling C.C., W.Va. | Wheeling Central Catholic High School | L 34-13 |
| 10/11 7 pm | at Carrick * | Cupples Stadium | L 18-12 |
| 10/18 12 pm | Brashear * | Cupples Stadium | L 33-14 |
| 10/24 7:30 pm | at Peabody * | Cupples Stadium | L 38-18 |
| 10/30 6 pm | at Belle Vernon | Belle Vernon | L 20-0 |
