| 2023-06-27 17:00:16June 27, 2023 |   First Round: Grace Brethren vs Annapolis Area Christian | 106 - 38 | Dematha-Court 1 |
| 2023-06-27 17:20:04June 27, 2023 |   First Round: Tech Prep vs Spalding | 64 - 68 | Dematha-Court 2 |
| 2023-06-27 18:20:57June 27, 2023 |   First Round: Fairfax Christian vs Landon | 59 - 57 | Dematha-Court 1 |
| 2023-06-27 18:40:58June 27, 2023 |   First Round: St. Stephen's & St. Agnes vs Cavaliers (W.T. Woodson) | 51 - 50 | Dematha-Court 2 |
| 2023-06-27 19:40:48June 27, 2023 |   First Round: Lanham Christian vs Patriot | 61 - 65 | Dematha-Court 1 |
| 2023-06-27 20:00:44June 27, 2023 |   First Round: Mt. Zion vs John Carroll | 58 - 56 | Dematha-Court 2 |
| 2023-06-27 21:00:24June 27, 2023 |   First Round: BCC vs Vikes (Whitman) | 60 - 64 | Dematha-Court 1 |
| 2023-06-27 21:20:38June 27, 2023 |   First Round: Sandy Spring vs Forest Park | 63 - 69 | Dematha-Court 2 |
| 2023-06-28 17:00:07June 28, 2023 |  Sweet 16: Mt. Zion vs. Tenley Tigers (Jackson Reed) | 69 - 60 | Dematha-Court 1 |
| 2023-06-28 17:20:39June 28, 2023 |  Sweet 16: Grace Brethren vs. Alexandria City | 75 - 78 | Dematha-Court 2 |
| 2023-06-28 18:20:52June 28, 2023 |  Sweet 16: St. Stephen's & St. Agnes vs McNamara | 47 - 75 | Dematha-Court 1 |
| 2023-06-28 18:40:19June 28, 2023 |  Sweet 16: Vikes (Whitman) vs. Riverdale Baptist | 70 - 59 | Dematha-Court 2 |
| 2023-06-28 19:40:27June 28, 2023 |  Sweet 16: Spalding vs. DeMatha | 60 - 59 | Dematha-Court 1 |
| 2023-06-28 20:00:24June 28, 2023 |  Sweet 16: Forest Park vs Brandywine Boyz (Gwynn Park) | 54 - 93 | Dematha-Court 2 |
| 2023-06-28 21:00:30June 28, 2023 |  Sweet 16: Patriot vs Bullis | 56 - 65 | Dematha-Court 1 |
| 2023-06-28 21:20:22June 28, 2023 |  Sweet 16: Fairfax Christian vs Cadets (Frederick) | 63 - 49 | Dematha-Court 2 |
| 2023-06-29 17:00:53June 29, 2023 | Quarterfinal: Cadets (Frederick) vs Riverdale Baptist | 61 - 72 | DeMatha-Main |
| 2023-06-29 18:20:46June 29, 2023 | Quarterfinal: St. Stephen's & St. Agnes vs Tenley Tigers (Jackson Reed) | 66 - 85 | DeMatha-Main |
| 2023-06-29 19:40:29June 29, 2023 | Quarterfinal: Brandywine Boyz (Gwynn Park) vs DeMatha | 39 - 73 | DeMatha-Main |
| 2023-06-29 21:00:01June 29, 2023 | Quarterfinal: Grace Brethren vs Bullis | 65 - 66 | DeMatha-Main |
| 2023-06-30 18:30:31June 30, 2023 | Semifinal: Riverdale Baptist vs DeMatha | 67 - 57 | DeMatha-Main |
| 2023-06-30 20:00:42June 30, 2023 | Semifinal: Tenley Tigers (Jackson Reed) vs Bullis | 57 - 41 | DeMatha-Main |
| 2023-07-01 14:30:00July 1, 2023 | Championship: DeMatha vs Jackson Reed (Tenley Tigers) | 64 - 62 | DeMatha-Main |
