| 2021-09-23 18:00:01September 23, 2021 | Football: Seed School @ H.D. Woodson | 0 - 40 | H.D. Woodson High School |
| 2021-09-24 15:30:29September 24, 2021 | Football: O'Connell @ Annapolis Area Christian | 32 - 6 | Annapolis Area Christian School |
| 2021-09-24 16:00:25September 24, 2021 | Football: Landon @ Woodberry Forest | 20 - 3 | Woodberry Forest School |
| 2021-09-24 16:00:39September 24, 2021 | Football: Loyola Blakefield @ Georgetown Prep | 24 - 6 | Georgetown Preparatory School |
| 2021-09-24 18:00:06September 24, 2021 | Football: Coolidge @ Bell Multicultural High School | 0 - 12 | Bell Multicultural High School |
| 2021-09-24 18:00:49September 24, 2021 | Football: Phelps vs. Ron Brown | 34 - 0 | Phelps High School |
| 2021-09-24 19:00:16September 24, 2021 | Football: McNamara @ St. Mary's Ryken | 20 - 14 | St. Mary's Ryken High School |
| 2021-09-24 19:00:32September 24, 2021 | Football: St. Albans @ Saint John Paul the Great Catholic | 47 - 3 | Saint John Paul the Great Catholic High School |
| 2021-09-24 19:00:41September 24, 2021 | Football: Gonzaga @ Archbishop Spalding | 13 - 20 | Archbishop Spalding High School |
| 2021-09-25 08:47:37September 25, 2021 | Football: Ballou vs. Carroll | 0 - 2 | Archbishop Carroll High School |
| 2021-09-25 12:00:07September 25, 2021 | Football: Maret @ Severn School | 44 - 6 | Jackson Reed High School |
| 2021-09-25 13:00:09September 25, 2021 | Football: Good Counsel @ Mount Saint Joseph | 29 - 21 | Mount Saint Joseph High School |
| 2021-09-25 13:00:29September 25, 2021 | Football: Collegiate School @ Flint Hill | 41 - 18 | Flint Hill School |
| 2021-09-25 13:00:39September 25, 2021 | Football: St. John's @ Archbishop Wood (PA) | 38 - 0 | Archbishop Wood High School |
| 2021-09-25 13:00:55September 25, 2021 | Football: Anacostia @ McKinley Tech | 26 - 8 | McKinley Technology High School |
| 2021-09-25 14:00:24September 25, 2021 | Football: Paul VI @ Saint James | 43 - 42 | Saint James School |
| 2021-09-25 14:00:51September 25, 2021 | Football: Ballou @ Carroll | 0 - 2 | Archbishop Carroll High School |
| 2021-09-25 14:00:57September 25, 2021 | Football: Ireton @ St. Stephen's & St. Agnes | 0 - 48 | St. Stephen's & St. Agnes School |
| 2021-09-25 14:00:58September 25, 2021 | Football: Trinity Episcopal @ Episcopal | 19 - 20 | Episcopal High School |
| 2021-09-25 19:00:39September 25, 2021 | Football: Avalon School @ Bullis | 48 - 10 | Bullis School |
