| USL | 07/07/19 | Saint Louis FC | - | Loudoun United | 2:2 |  |
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| USL | 10/10/19 | Loudoun United | - | Saint Louis FC | 4:3 |  |
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| 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 | |
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| USL | 24/10/21 | Loudoun United | - | Tampa Bay Rowdies | 0:1 | |
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| USL | 17/07/22 | Loudoun United | - | Tampa Bay Rowdies | 1:4 | ||||
| USL | 09/10/22 | Tampa Bay Rowdies | - | Loudoun United | 8:0 | ||||
| USL | 01/10/23 | Tampa Bay Rowdies | - | Loudoun United | 1:0 | ||||
| USL | 30/06/24 | Loudoun United | - | Tampa Bay Rowdies | 2:0 | ||||
| USL | 18/08/24 | Tampa Bay Rowdies | - | Loudoun United | 0:2 |
England