| 2021-10-22 12:00:12October 22, 2021 | Football: Sidwell Friends @ Maret | 14 - 22 | The St. James Sports Complex |
| 2021-10-22 18:00:09October 22, 2021 | Football: Wilson @ Eastern | 55 - 0 | Eastern High School |
| 2021-10-22 18:00:21October 22, 2021 | Football: Anacostia @ Phelps | 44 - 0 | Phelps High School |
| 2021-10-22 18:00:22October 22, 2021 | Football: McKinley Tech @ Bell Multicultural High School | 24 - 52 | Bell Multicultural High School |
| 2021-10-22 18:00:35October 22, 2021 | Football: Theodore Roosevelt @ Ballou | 68 - 12 | Ballou High School |
| 2021-10-22 18:00:46October 22, 2021 | Football: Dunbar @ H. D. Woodson | 26 - 20 | H.D. Woodson High School |
| 2021-10-22 19:00:02October 22, 2021 | Football: Episcopal @ Bullis | 0 - 21 | Bullis School |
| 2021-10-22 19:00:07October 22, 2021 | Football: St. John's @ DeMatha | 14 - 7 | DeMatha High School |
| 2021-10-22 19:00:39October 22, 2021 | Football: McNamara @ Good Counsel | 9 - 30 | Good Counsel High School |
| 2021-10-23 13:00:27October 23, 2021 | Football: Paul VI @ Bishop Ireton | 49 - 13 | Bishop Ireton High School |
| 2021-10-23 14:00:24October 23, 2021 | Football: Norfolk Academy @ Flint Hill | 38 - 7 | Flint Hill School |
| 2021-10-23 14:00:41October 23, 2021 | Football: St. Stephen's & St. Agnes @ St. Albans | 14 - 6 | St. Albans School |
| 2021-10-23 14:00:44October 23, 2021 | Football: O'Connell @ Carroll | 0 - 54 | Archbishop Carroll High School |
| 2021-10-23 14:30:31October 23, 2021 | Football: Potomac School @ St. James School | 14 - 36 | Saint James School |
| 2021-10-23 15:00:52October 23, 2021 | Football: Landon @ Georgetown Prep | 7 - 28 | Georgetown Preparatory School |
| 2021-10-23 15:00:55October 23, 2021 | Football: Cardozo @ Coolidge | 0 - 65 | Coolidge High School |
