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| Date | Match | Score |
|---|---|---|
| 23.05.2026 | Loudoun United - Detroit City | 0 : 0 |
| 11.10.2025 | Detroit City - Loudoun United | 0 : 1 |
| 14.06.2025 | Loudoun United - Detroit City | 3 : 2 |
| 04.05.2024 | Loudoun United - Detroit City | 0 : 0 |
| 23.03.2024 | Detroit City - Loudoun United | 2 : 1 |
| 07.10.2023 | Loudoun United - Detroit City | 0 : 3 |
| 12.07.2023 | Detroit City - Loudoun United | 1 : 1 |
| 01.10.2022 | Loudoun United - Detroit City | 0 : 4 |
| 14.05.2022 | Detroit City - Loudoun United | 4 : 2 |
| Date | Match | Score | Res |
|---|---|---|---|
| 05.09.2026 | Loudoun United - Colorado Springs | 4 - 5 | L |
| 30.08.2026 | El Paso Locomotive - Loudoun United | 4 - 1 | L |
| 22.08.2026 | Loudoun United - New Mexico United | 0 - 0 | D |
| 15.08.2026 | Detroit City - Loudoun United | 0 - 0 | D |
| 08.08.2026 | Loudoun United - Charleston Battery | 0 - 1 | L |
| Date | Match | Score | Res |
|---|---|---|---|
| 05.09.2026 | Detroit City - Hartford Athletic | 1 - 1 | D |
| 30.08.2026 | Louisville City - Detroit City | 0 - 0 | D |
| 22.08.2026 | Detroit City - Tampa Bay Rowdies | 1 - 0 | W |
| 15.08.2026 | Detroit City - Loudoun United | 0 - 0 | D |
| 09.08.2026 | FC Tulsa - Detroit City | 0 - 1 | W |