| qua, 3 de jun.. | Annapolis Blues  v  Lionsbridge | 20:00 | USL League Two | |
| sáb, 6 de jun.. | Annapolis Blues v  Patuxent | 20:00 | USL League Two | |
| qua, 10 de jun.. | Loudoun 2  v Annapolis Blues | 20:30 | USL League Two | |
| seg, 15 de jun.. | Christos  v Annapolis Blues | 20:00 | USL League Two | |
| qua, 17 de jun.. | Annapolis Blues v  Hill City | 20:00 | USL League Two | |
| dom, 21 de jun.. | Annapolis Blues v  Evergreen | 20:30 | USL League Two | |
| ter, 23 de jun.. | Annapolis Blues v  Santos Laguna | 20:00 | Friendlies Clubs | |
| qua, 24 de jun.. | Bethesda SC  v Annapolis Blues | 20:30 | USL League Two | |
| sáb, 27 de jun.. | Annapolis Blues v Christos | 20:30 | USL League Two | |
| ter, 30 de jun.. | Virginia Marauders  v Annapolis Blues | 20:30 | USL League Two | |
v 