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| Date | Match | Score |
|---|---|---|
| 11.04.2024 | Philadelphia Union II - Orlando City II | 1 : 1 |
| 28.06.2023 | Orlando City II - Philadelphia Union II | 0 : 3 |
| 26.03.2023 | Philadelphia Union II - Orlando City II | 1 : 3 |
| 11.09.2022 | Philadelphia Union II - Orlando City II | 6 : 1 |
| 24.07.2022 | Orlando City II - Philadelphia Union II | 1 : 3 |
| 16.05.2022 | Philadelphia Union II - Orlando City II | 1 : 0 |
| 31.08.2017 | Orlando City II - Philadelphia Union II | 1 : 1 |
| 23.04.2017 | Philadelphia Union II - Orlando City II | 0 : 2 |
| 25.09.2016 | Philadelphia Union II - Orlando City II | 0 : 2 |
| 07.05.2016 | Orlando City II - Philadelphia Union II | 2 : 2 |
| Date | Match | Score | Res |
|---|---|---|---|
| 04.09.2026 | Inter Miami II - Orlando City II | 1 - 4 | W |
| 30.08.2026 | Orlando City II - Crown Legacy | 3 - 2 | W |
| 22.08.2026 | Atlanta United II - Orlando City II | 5 - 1 | L |
| 15.08.2026 | Chicago Fire II - Orlando City II | 2 - 0 | L |
| 11.08.2026 | New York City II - Orlando City II | 3 - 0 | L |
| Date | Match | Score | Res |
|---|---|---|---|
| 04.09.2026 | Philadelphia Union II - Columbus Crew II | 1 - 0 | W |
| 30.08.2026 | FC Cincinnati II - Philadelphia Union II | 2 - 3 | W |
| 23.08.2026 | Philadelphia Union II - Connecticut FC | 2 - 4 | L |
| 16.08.2026 | New England II - Philadelphia Union II | 3 - 4 | W |
| 08.08.2026 | Philadelphia Union II - FC Cincinnati II | 2 - 1 | W |