| 2019-10-12 19:10:02October 12, 2019 | Westmont White vs Penn Highlands Boys | 12 - 2 | EHR Main Gym |
| 2019-10-13 12:30:02October 13, 2019 | JCS vs Penn Highlands Boys | 32 - 2 | RHS Aux Gym |
| 2019-10-18 18:35:02October 18, 2019 | Penn Highlands Boys vs Forest Hills- Cambria Health Services | 20 - 5 | EHR Aux Gym |
| 2019-10-20 19:00:02October 20, 2019 | Penn Highlands Boys vs Down To Earth Lawncare | 2 - 26 | RHS Aux Gym |
| 2019-10-26 18:05:02October 26, 2019 | Benscreek Club vs Penn Highlands Boys | 20 - 8 | EHR Main Gym |
| 2019-11-03 11:25:02November 3, 2019 | Penn Highlands Boys vs Shanksville Vikings | 0 - 36 | EHR Main Gym |
| 2019-11-05 17:30:02November 5, 2019 | Penn Highlands Boys vs Riches Towing | 9 - 24 | EHR Aux Gym |
| 2019-11-16 19:10:02November 16, 2019 | Windber 3 vs Penn Highlands Boys | 30 - 8 | EHR Main Gym |
| 2019-11-23 17:00:02November 23, 2019 | Penn Highlands Boys vs Ferndale Sportsmen’s | 5 - 32 | EHR Main Gym |
| 2019-11-24 13:35:02November 24, 2019 | Penn Highlands Boys vs Morris Tavern FH | 3 - 29 | RHS Aux Gym |
| 2019-12-01 16:50:02December 1, 2019 | JCS vs Penn Highlands Boys | 34 - 10 | RHS Aux Gym |
| 2019-12-05 19:40:02December 5, 2019 | Westmont White vs Penn Highlands Boys | 16 - 2 | EHR Main Gym |
