| 2023-09-02 14:00:58September 2, 2023 | Football: Flint Hill vs. Woodberry Forest | 2023 Football Season | Woodberry Forest School |
| 2023-09-08 18:30:54September 8, 2023 | Football: Flint Hill vs. St. Christopher's | 2023 Football Season | St. Christopher's School |
| 2023-09-16 13:00:27September 16, 2023 | Football: Benedictine vs. Flint Hill | 2023 Football Season | Flint Hill School |
| 2023-09-23 13:00:28September 23, 2023 | Football: Flint Hill vs. St. Stephen's & St. Agnes | 2023 Football Season | St. Stephen's & St. Agnes School |
| 2023-10-20 17:30:03October 20, 2023 | Football: Collegiate vs. Flint Hill | 2023 Football Season | Flint Hill School |
| 2023-10-27 19:00:45October 27, 2023 | Football: Flint Hill vs. Maret | 2023 Football Season | Maret School |
| 2023-11-04 12:30:36November 4, 2023 | Football: St. James vs. Flint Hill | 2023 Football Season | Flint Hill School |
