| 2023-09-08 16:00:10September 8, 2023 | Football: St. Paul's vs. Landon | 0 - 24 | IAC Football | 2023 Football Season | Landon School |
| 2023-09-08 18:30:54September 8, 2023 | Football: Flint Hill vs. St. Christopher's | 13 - 27 | MAC Football | 2023 Football Season | St. Christopher's School |
| 2023-09-08 19:00:05September 8, 2023 | Football: Maret vs. St. Stephen's & St. Agnes | 51 - 17 | IAC Football, MAC Football | 2023 Football Season | St. Stephen's & St. Agnes School |
| 2023-09-08 19:00:12September 8, 2023 | Football: Loyola Blakefield vs. Georgetown Prep | 7 - 23 | IAC Football | 2023 Football Season | Georgetown Preparatory School |
| 2023-09-08 19:00:25September 8, 2023 | Football: Life Christian Academy vs. Good Counsel | 19:00:25Canceled | WCAC Upper Division | 2023 Football Season | Good Counsel High School |
| 2023-09-08 19:00:43September 8, 2023 | Football: Gonzaga vs. Fordham Prep (NY) | 45 - 0 | WCAC Upper Division | 2023 Football Season | Fordham Preparatory School |
| 2023-09-09 12:00:49September 9, 2023 | Football: St. John's vs. Erasmus Hall (NY) | 12:00:49Canceled | WCAC Upper Division | 2023 Football Season | Erasmus Hall High School |
| 2023-09-09 12:00:58September 9, 2023 | Football: St. Albans vs. O'Connell | 0 - 2 | IAC Football, WCAC Lower Division | 2023 Football Season | Bishop O'Connell High School |
| 2023-09-09 13:00:05September 9, 2023 | Football: St. Mary's Ryken vs. Mount St. Joseph | 42 - 7 | WCAC Lower Division | 2023 Football Season | Mount Saint Joseph High School |
| 2023-09-09 13:00:37September 9, 2023 | Football: Riverdale Baptist vs. McNamara | 14 - 17 | WCAC Upper Division | 2023 Football Season | Bishop McNamara High School |
| 2023-09-09 13:30:13September 9, 2023 | Football: DeMatha vs. Freedom (VA) | 7 - 7 | WCAC Upper Division | 2023 Football Season | Freedom High School |
| 2023-09-09 14:00:13September 9, 2023 | Football: St. James vs. Kiski School (PA) | 31 - 0 | MAC Football | 2023 Football Season | The Kiski School |
| 2023-09-11 16:00:46September 11, 2023 | Football: St. Michael the Archangel vs. Episcopal | 22 - 26 | IAC Football | 2023 Football Season | Episcopal High School |
| 2023-09-11 18:00:33September 11, 2023 | Football: Potomac School vs. Paul VI | 0 - 28 | MAC Football, WCAC Lower Division | 2023 Football Season | Paul VI High School |
