| 2021-09-03 15:30:18September 3, 2021 | Football: O'Connell @ St. Stephen's & St. Agnes | 0 - 12 | St. Stephen's & St. Agnes School |
| 2021-09-11 12:00:58September 11, 2021 | Football: Archbishop Curley @ O'Connell | 31 - 10 | Bishop O'Connell High School |
| 2021-09-18 12:00:05September 18, 2021 | Football: St. John's Catholic Prep @ O'Connell | 6 - 22 | Bishop O'Connell High School |
| 2021-09-24 15:30:29September 24, 2021 | Football: O'Connell @ Annapolis Area Christian | 32 - 6 | Annapolis Area Christian School |
| 2021-10-02 12:00:48October 2, 2021 | Football: Annandale @ O'Connell | 6 - 30 | Bishop O'Connell High School |
| 2021-10-09 13:00:23October 9, 2021 | Football: St. Mary's Ryken @ O'Connell | 30 - 0 | Bishop O'Connell High School |
| 2021-10-16 13:30:09October 16, 2021 | Football: Ireton @ O'Connell | 14 - 15 | Bishop O'Connell High School |
| 2021-10-23 14:00:44October 23, 2021 | Football: O'Connell @ Carroll | 0 - 54 | Archbishop Carroll High School |
| 2021-10-30 12:00:29October 30, 2021 | Football: Saint John Paul the Great @ O'Connell | 13 - 25 | Bishop O'Connell High School |
| 2021-11-05 19:00:30November 5, 2021 | Football: O'Connell @ Paul VI | 3 - 23 | Paul VI High School |
| 2021-11-13 01:00:00November 13, 2021 | WCAC Football Playoffs: O’Connell @ Carroll | 0 - 54 | Archbishop Carroll High School |
| 2021-11-13 13:00:00November 13, 2021 | O’Connell Football vs Carroll Football | 0 - 54 | |
