IHSA have released the football schedule for the 2016 season. Cumberland’s schedule is below. Listen to Cumberland Pirate Football on WCRA 96.3 and 99.5 FM.
Cumberland High School Football Schedule
| Date | Time | Home/Away | Opponent |
| Aug 26 | 7:00 | Home | Decatur Lutheran |
| Sep 2 | 7:00 | Home | Sullivan |
| Sep 9 | 7:00 | Home | Niantic |
| Sep 16 | 7:00 | Home | Martinsville |
| Sep 23 | 7:00 | Away | Palestine |
| Sep 30 | 7:00 | Away | Oblong |
| Oct 7 | 7:00 | Home | Oakland |
| Oct 14 | 7:00 | Away | Villa Grove |
| Oct 21 | 7:00 | Away | Argenta |
