| USL | 20/04/19 | New York RB II | - | Loudoun United | 1:3 | ||||
| USL | 20/10/19 | Loudoun United | - | New York RB II | 7:3 | ||||
| USL | 12/06/21 | Tampa Bay Rowdies | - | Loudoun United | 2:1 | ||||
| USL | 25/07/21 | Tampa Bay Rowdies | - | Loudoun United | 3:1 | ||||
| USL | 24/08/21 | Loudoun United | - | Tampa Bay Rowdies | 0:2 | ||||
| USL | 24/10/21 | Loudoun United | - | Tampa Bay Rowdies | 0:1 | ||||
| USL | 09/10/22 | Tampa Bay Rowdies | - | Loudoun United | 8:0 | ||||
| USL | 04/07/24 | Loudoun United | - | Hartford Athletic | 3:0 |  |
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| USL | 05/04/25 | Loudoun United | - | Hartford Athletic | 2:0 |
Jamaica