2021 Varsity Football Schedule
| Day | Date | Opponent | Location | Time | Score |
| Tuesday | August 17 | Green Street Academy (scrimmage) |
CPS | 5:30 pm | |
| Friday | August 27 | McDonogh (scrimmage) | CPS | 4:00 pm | |
| Friday | September 3 | Curley | Curley | 4:00 pm | W, 14-2 |
| Friday | September 10 | John Carroll | CPS | 4:00 pm | W, 47-0 |
| Friday | September 17 | Avalon | CPS | 4:00 pm | L, 14-12 |
| Saturday | September 25 | Boys Latin | CPS | 12:00 pm | W, 38-10 |
| Cancelled | |||||
| Saturday | October 9 | Mt. Carmel | Mt. Carmel (Eastern Regional Park) | 7:00 pm | W, 14-6 |
| Saturday | October 16 | St. Paul’s (Homecoming) |
CPS | 1:00 pm | W, 17-12 |
| Saturday | October 23 | St. Mary’s | CPS | 12:00 pm | W, 23-17 |
| Saturday | October 30 | Gilman (Senior Game) |
CPS | 4:00 pm | W, 20-6 |
| Saturday | November 6 | Loyola | Loyola | 2:30 pm | L, 41-9 |
| Saturday | November 13 | MIAA Semi Finals vs. St. Mary’s | CPS | 12:00 pm | W, 8-0 |
| Friday/Saturday | November 20/21 | MIAA Championships vs. Loyola Blakefield | Calvert Hall | 7:00 pm | W, 14-5 |
