| 2021-09-17 18:00:24September 17, 2021 | Football: Carroll @ Wilson | 43 - 0 | Jackson Reed High School |
| 2021-09-17 18:00:26September 17, 2021 | Football: Landon @ McKinley Tech | 41 - 0 | McKinley Technology High School |
| 2021-09-17 18:00:43September 17, 2021 | Football: Bell Multicultural High School @ Eastern | 2 - 0 | Eastern High School |
| 2021-09-17 18:00:54September 17, 2021 | Football: Coolidge @ Dunbar | 7 - 28 | Dunbar High School |
| 2021-09-17 18:00:59September 17, 2021 | Football: Woodberry Forest @ Georgetown Prep | 21 - 34 | Georgetown Preparatory School |
| 2021-09-17 19:00:10September 17, 2021 | Football: St. Frances Academy @ Good Counsel | 50 - 7 | Good Counsel High School |
| 2021-09-17 19:00:13September 17, 2021 | Football: St. James School @ Williamsport High School | 41 - 13 | Williamsport High School |
| 2021-09-17 19:00:14September 17, 2021 | Football: DeMatha @ Friendship Collegiate | 38 - 0 | Friendship Collegiate |
| 2021-09-17 19:00:15September 17, 2021 | Football: Urbana @ St. Mary's Ryken | 27 - 45 | St. Mary's Ryken High School |
| 2021-09-17 19:00:22September 17, 2021 | Football: Sidwell Friends @ Saint John Paul the Great | 13 - 7 | Saint John Paul the Great Catholic High School |
| 2021-09-17 19:00:26September 17, 2021 | Football: Ballou @ Paul VI | 8 - 43 | Paul VI High School |
| 2021-09-17 19:00:26September 17, 2021 | Football: Gonzaga @ St. Joseph Prep (PA) | 3 - 38 | St. Joseph's Preparatory School |
| 2021-09-17 19:00:30September 17, 2021 | Football: Broadneck @ Bullis | 38 - 7 | Bullis School |
| 2021-09-18 11:00:51September 18, 2021 | Football: McNamara @ H.D. Woodson | 22 - 0 | H.D. Woodson High School |
| 2021-09-18 12:00:05September 18, 2021 | Football: St. John's Catholic Prep @ O'Connell | 6 - 22 | Bishop O'Connell High School |
| 2021-09-18 12:00:13September 18, 2021 | Football: Maret @ Richard Wright | 58 - 12 | Jackson Reed High School |
| 2021-09-18 13:00:19September 18, 2021 | Football: Chesapeake @ Theodore Roosevelt | 26 - 29 | Theodore Roosevelt High School |
| 2021-09-18 13:00:58September 18, 2021 | Football: St. Stephen's & St. Agnes @ Flint Hill | 49 - 0 | Flint Hill School |
| 2021-09-18 13:30:56September 18, 2021 | Football: Potomac School @ Ireton | 21 - 7 | Bishop Ireton High School |
| 2021-09-18 14:00:14September 18, 2021 | Football: St. Christopher's @ St. Albans | 37 - 6 | St. Albans School |
| 2021-09-18 14:00:41September 18, 2021 | Football: Life Christian Academy (VA) @ St. John's | 0 - 31 | St. John's College High School |
