| 2023-10-20 17:30:03October 20, 2023 | Football: Collegiate vs. Flint Hill | 7 - 28 | 2023 Football Season | Flint Hill School |
| 2023-10-20 19:00:00October 20, 2023 | Football: St. John's vs. DeMatha | 14 - 21 | 2023 Football Season | DeMatha High School |
| 2023-10-20 19:00:13October 20, 2023 | Football: St. Mary's Ryken vs. St. John Paul the Great Catholic | 49 - 6 | 2023 Football Season | Saint John Paul the Great Catholic High School |
| 2023-10-21 12:00:45October 21, 2023 | Football: St. James vs. Executive Education Academy Charter School | 49 - 8 | 2023 Football Season | Executive Education Academy Charter School |
| 2023-10-21 13:00:20October 21, 2023 | Football: Paul VI vs. Ireton | 14 - 26 | 2023 Football Season | Bishop Ireton High School |
| 2023-10-21 13:00:48October 21, 2023 | Football: Gonzaga vs. McNamara | 17 - 9 | 2023 Football Season | Bishop McNamara High School |
| 2023-10-21 14:00:02October 21, 2023 | Football: St. Albans vs. Episcopal | 0 - 21 | 2023 Football Season | Episcopal High School |
| 2023-10-21 14:00:15October 21, 2023 | Football: O'Connell vs. Carroll | 3 - 13 | 2023 Football Season | Archbishop Carroll High School |
| 2023-10-21 14:00:30October 21, 2023 | Football: Bullis vs. St. Stephen's & St. Agnes | 28 - 10 | 2023 Football Season | St. Stephen's & St. Agnes School |
| 2023-10-21 14:00:57October 21, 2023 | Football: Landon vs. Georgetown Prep | 21 - 24 | 2023 Football Season | Georgetown Preparatory School |
| 2023-10-21 14:30:30October 21, 2023 | Football: Potomac School vs. Maret | 21 - 43 | 2023 Football Season | Maret School |
