| USL | 29/07/19 | Loudoun United | - | Louisville City FC | 3:0 | ||||
| USL | 16/08/20 | Louisville City FC | - | Loudoun United | 2:0 | ||||
| USL | 03/05/21 | Miami FC | - | Loudoun United | 2:1 | ||||
| USL | 26/09/21 | Miami FC | - | Loudoun United | 6:1 | ||||
| USL | 24/07/22 | Loudoun United | - | Miami FC | 1:2 | ||||
| USL | 01/04/23 | Loudoun United | - | Colorado Springs Switchbacks | 0:1 |  |
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| USL | 29/09/24 | Colorado Springs Switchbacks | - | Loudoun United | 1:1 | ||||
| USL | 10/05/25 | Loudoun United | - | Lexington SC | 5:1 |
Jamaica