| 2023-09-14 16:30:54September 14, 2023 | Football: Severn vs. Maret | 21 - 43 | MAC Football | Maret School |
| 2023-09-14 19:00:48September 14, 2023 | Football: Roosevelt vs. Bullis | 8 - 28 | IAC Football, Stars Division | Bullis School |
| 2023-09-15 16:30:39September 15, 2023 | Football: Ireton vs. St. Stephen's & St. Agnes | 28 - 17 | IAC Football, WCAC Lower Division | St. Stephen's & St. Agnes School |
| 2023-09-15 18:00:34September 15, 2023 | Football: Woodberry Forest vs. Georgetown Prep | 25 - 28 | IAC Football | Georgetown Preparatory School |
| 2023-09-15 19:00:03September 15, 2023 | Football: Gonzaga vs. Loyola Blakefield | 29 - 35 | WCAC Upper Division | Loyola Blakefield |
| 2023-09-15 19:00:07September 15, 2023 | Football: Carroll vs. St. Mary's Annapolis | 15 - 20 | WCAC Lower Division | St. Mary's School |
| 2023-09-15 19:00:18September 15, 2023 | Football: Trinity Episcopal vs. St. Mary's Ryken | 35 - 6 | WCAC Lower Division | St. Mary's Ryken High School |
| 2023-09-15 19:00:21September 15, 2023 | Football: St. Michael the Archangel vs. Paul VI | 28 - 0 | WCAC Lower Division | Paul VI High School |
| 2023-09-15 19:00:42September 15, 2023 | Football: Roman Catholic (PA) vs. DeMatha | 23 - 25 | WCAC Upper Division | DeMatha High School |
| 2023-09-15 19:00:57September 15, 2023 | Football: McNamara vs. Moody (AL) | 14 - 10 | WCAC Upper Division | Moody High School |
| 2023-09-16 12:00:07September 16, 2023 | Football: John Carroll vs. O'Connell | 22 - 13 | WCAC Lower Division | Bishop O'Connell High School |
| 2023-09-16 13:00:18September 16, 2023 | Football: Good Counsel vs. Mount St. Joseph | 38 - 8 | WCAC Upper Division | Mount Saint Joseph High School |
| 2023-09-16 13:00:27September 16, 2023 | Football: Benedictine vs. Flint Hill | 41 - 6 | MAC Football | Flint Hill School |
| 2023-09-16 13:00:53September 16, 2023 | Football: Gray Collegiate Academy vs. St. John's | 28 - 42 | WCAC Upper Division | St. John's College High School |
| 2023-09-16 14:00:04September 16, 2023 | Football: St. James vs. Our Lady of Mount Carmel | 28 - 21 | MAC Football | Our Lady of Mount Carmel |
| 2023-09-16 14:00:44September 16, 2023 | Football: St. Albans vs. Jackson Reed | 40 - 3 | IAC Football, Stars Division | Jackson Reed High School |
