| MLS | 04/07/19 | Orlando City | - | Philadelphia Union | 1:3 |  |
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| MLS | 21/07/20 | Philadelphia Union | - | Orlando City | 1:1 | ||||
| MLS | 23/07/21 | Orlando City | - | Philadelphia Union | 2:1 | ||||
| MLS | 19/09/21 | Philadelphia Union | - | Orlando City | 3:1 |  |
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| Open Cup | 11/05/22 | Orlando City | - | Philadelphia Union | 2:1 | ||||
| MLS | 24/07/22 | Orlando City | - | Philadelphia Union | 0:1 | ||||
| MLS | 25/03/23 | Philadelphia Union | - | Orlando City | 1:2 | ||||
| MLS | 22/06/23 | Orlando City | - | Philadelphia Union | 2:2 | ||||
| MLS | 12/05/24 | Philadelphia Union | - | Orlando City | 2:3 | ||||
| MLS | 03/10/24 | Orlando City | - | Philadelphia Union | 2:1 | ||||
| MLS | 23/02/25 | Orlando City | - | Philadelphia Union | 2:4 | ||||
| MLS | 06/04/25 | Philadelphia Union | - | Orlando City | 0:0 | |
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