[5] Orlando City SC II 0-3 Philadelphia Union II [10] 2023-06-28 23:00
Stadion: Osceola County Stadium Round: 1
Head to Head
| USA - MLS Next Pro League | 2023/03/26 19:00 | Philadelphia Union II v Orlando City II | W | 1-3 |
| USA - MLS Next Pro League | 2022/09/11 17:00 | Philadelphia Union II v Orlando City II | L | 6-1 |
| USA - MLS Next Pro League | 2022/07/24 23:00 | Orlando City II v Philadelphia Union II | L | 1-3 |
| USA - MLS Next Pro League | 2022/05/16 23:00 | Philadelphia Union II v Orlando City II | L | 1-0 |
| USA - USL Championship | 2017/08/31 23:30 | Orlando City II v Philadelphia Union II | D | 1-1 |
| USA - USL Championship | 2017/04/23 20:00 | Philadelphia Union II v Orlando City II | W | 0-2 |
| USA - USL Championship | 2016/09/25 19:00 | Philadelphia Union II v Orlando City II | W | 0-2 |
| USA - USL Championship | 2016/05/07 23:30 | Orlando City II v Philadelphia Union II | D | 2-2 |
Home History
| USA - MLS Next Pro League | 2023/06/16 00:00 | Chicago Fire II v Orlando City II | L | 1-0 |
| USA - MLS Next Pro League | 2023/06/11 22:00 | Orlando City II v FC Cincinnati II | W | 4-0 |
| USA - MLS Next Pro League | 2023/05/29 23:00 | Orlando City II v New York Red Bulls II | W | 3-2 |
| USA - MLS Next Pro League | 2023/05/25 23:00 | Inter Miami CF II v Orlando City II | W | 0-1 |
| USA - MLS Next Pro League | 2023/05/19 23:00 | Orlando City II v Atlanta United II | L | 6-7 |
| USA - MLS Next Pro League | 2023/05/14 18:00 | Columbus Crew II v Orlando City II | L | 4-0 |
| USA - MLS Next Pro League | 2023/05/05 23:30 | Crown Legacy v Orlando City II | L | 3-2 |
| USA - MLS Next Pro League | 2023/04/30 22:00 | Orlando City II v Toronto FC ll | W | 3-2 |
Away History
| USA - MLS Next Pro League | 2023/06/18 22:00 | Philadelphia Union II v Chicago Fire II | L | 2-5 |
| USA - MLS Next Pro League | 2023/06/14 23:00 | Philadelphia Union II v Crown Legacy | L | 0-2 |
| USA - MLS Next Pro League | 2023/06/09 23:00 | Philadelphia Union II v Atlanta United II | W | 1-0 |
| USA - MLS Next Pro League | 2023/06/04 22:00 | FC Cincinnati II v Philadelphia Union II | L | 2-1 |
| USA - MLS Next Pro League | 2023/05/28 23:00 | Philadelphia Union II v Columbus Crew II | W | 3-2 |
| USA - MLS Next Pro League | 2023/05/24 23:00 | Crown Legacy v Philadelphia Union II | L | 6-4 |
| USA - MLS Next Pro League | 2023/05/21 19:00 | Philadelphia Union II v New England Revolution II | L | 3-4 |
| USA - MLS Next Pro League | 2023/05/14 22:00 | Inter Miami CF II v Philadelphia Union II | W | 5-6 |