| 2023-08-26 14:30:36August 26, 2023 | Football: Virginia Academy vs. O'Connell | 7 - 10 | 2023 Football Season | Bishop O'Connell High School |
| 2023-09-01 19:00:37September 1, 2023 | Football: O'Connell vs. St. Stephen's & St. Agnes | 14 - 31 | 2023 Football Season | St. Stephen's & St. Agnes School |
| 2023-09-09 12:00:58September 9, 2023 | Football: St. Albans vs. O'Connell | 0 - 2 | 2023 Football Season | Bishop O'Connell High School |
| 2023-09-16 12:00:07September 16, 2023 | Football: John Carroll vs. O'Connell | 22 - 13 | 2023 Football Season | Bishop O'Connell High School |
| 2023-09-23 13:00:12September 23, 2023 | Football: O'Connell vs. Annapolis Area Christian | 13:00:12Canceled | 2023 Football Season | Annapolis Area Christian School |
| 2023-10-07 14:00:31October 7, 2023 | Football: St. John Paul the Great Catholic vs. O'Connell | 14:00:312:00 pm | 2023 Football Season | Bishop O'Connell High School |
| 2023-10-14 12:00:22October 14, 2023 | Football: St. Mary's Ryken vs. O'Connell | 12:00:2212:00 pm | 2023 Football Season | Bishop O'Connell High School |
| 2023-10-21 14:00:15October 21, 2023 | Football: O'Connell vs. Carroll | 14:00:152:00 pm | 2023 Football Season | Archbishop Carroll High School |
| 2023-10-28 12:00:14October 28, 2023 | Football: Ireton vs. O'Connell | 12:00:1412:00 pm | 2023 Football Season | Bishop O'Connell High School |
| 2023-11-03 19:00:14November 3, 2023 | Football: O'Connell vs. Paul VI | 19:00:147:00 pm | 2023 Football Season | Paul VI High School |
