Team schedule for 2008-2009 Highlands football
Conference record: 5-0-0 Overall: 11-1-0
WPIAL - Greater Allegheny Conference
* Conference games | PPD Postponed | F Forfeit
| Date | Opponent | Venue | Score |
|---|---|---|---|
| 8/29 7 pm | at Fox Chapel | Fox Chapel | W 24-16 |
| 9/5 7:30 pm | at Montour | Montour | W 20-12 |
| 9/12 7:30 pm | Pine-Richland | Highlands | W 14-0 |
| 9/19 7:30 pm | at Kiski Area | Davis Field, Vandergrift | W 48-31 |
| 9/25 7 pm | at Mars * | Mars | W 26-7 |
| 10/3 7:30 pm | Indiana * | Highlands | W 21-14 |
| 10/10 7:30 pm | Franklin Regional * | Highlands | W 10-7 |
| 10/17 7:30 pm | at Knoch * | Knoch | W 35-18 |
| 10/24 7:30 pm | Hampton * | Highlands | W 41-7 |
| WPIAL Class AAA Playoffs: First Round | |||
| 10/31 7:30 pm | Laurel Highlands | Highlands | W 49-14 |
| WPIAL Class AAA Playoffs: Quarterfinals | |||
| 11/7 7:30 pm | Montour | Plum | W 35-34 |
| WPIAL Class AAA Playoffs: Semifinals | |||
| 11/14 7:30 pm | Blackhawk | North Hills | L 36-7 |
