[5] Orlando City SC II 3-2 Chicago Fire II [15] 2023-07-23 23:00
Stadium: Osceola County Stadium Round: 1
Head to Head
| 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 | 2022/07/17 23:00 | Chicago Fire II v Orlando City II | W | 3-4 |
| USA - MLS Next Pro League | 2022/03/26 19:00 | Orlando City II v Chicago Fire II | W | 2-0 |
Home History
| USA - MLS Next Pro League | 2023/07/16 23:00 | Orlando City II v Atlanta United II | W | 3-2 |
| USA - MLS Next Pro League | 2023/07/09 23:00 | Huntsville City v Orlando City II | L | 6-2 |
| USA - MLS Next Pro League | 2023/07/02 23:00 | FC Cincinnati II v Orlando City II | W | 3-5 |
| USA - MLS Next Pro League | 2023/06/28 23:00 | Orlando City II v Philadelphia Union II | L | 0-3 |
| 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 |
Away History
| USA - MLS Next Pro League | 2023/07/16 23:00 | New York City FC II v Chicago Fire II | W | 3-5 |
| USA - MLS Next Pro League | 2023/07/09 22:00 | Chicago Fire II v FC Cincinnati II | L | 3-4 |
| USA - MLS Next Pro League | 2023/07/03 00:35 | Chicago Fire II v Columbus Crew II | W | 2-0 |
| USA - MLS Next Pro League | 2023/06/25 21:00 | Crown Legacy v Chicago Fire II | L | 4-2 |
| USA - MLS Next Pro League | 2023/06/18 22:00 | Philadelphia Union II v Chicago Fire II | W | 2-5 |
| USA - MLS Next Pro League | 2023/06/16 00:00 | Chicago Fire II v Orlando City II | W | 1-0 |
| USA - MLS Next Pro League | 2023/06/12 00:00 | New England Revolution II v Chicago Fire II | L | 6-5 |
| USA - MLS Next Pro League | 2023/06/04 18:00 | Columbus Crew II v Chicago Fire II | W | 2-4 |