[5] Orlando City II 4-1 Columbus Crew II [6] 2023-08-27 23:00
Stadium: Osceola County Stadium Round: 1
Head to Head
| 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 | 2022/08/20 23:00 | Orlando City II v Columbus Crew II | D | 2-2 |
| USA MLS Next Pro League | 2022/06/19 18:00 | Columbus Crew II v Orlando City II | L | 6-1 |
| USA MLS Next Pro League | 2022/04/15 23:00 | Columbus Crew II v Orlando City II | L | 2-0 |
Home History
| USA MLS Next Pro League | 2023/08/13 23:00 | New York City FC II v Orlando City II | W | 3-4 |
| USA MLS Next Pro League | 2023/08/09 22:00 | Orlando City II v New England Revolution II | L | 4-5 |
| USA MLS Next Pro League | 2023/08/05 22:00 | Inter Miami CF II v Orlando City II | D | 1-1 |
| USA MLS Next Pro League | 2023/07/31 23:00 | New York Red Bulls II v Orlando City II | L | 2-1 |
| USA MLS Next Pro League | 2023/07/23 23:00 | Orlando City II v Chicago Fire II | W | 3-2 |
| 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 |
Away History
| USA MLS Next Pro League | 2023/08/19 22:00 | Columbus Crew II v FC Cincinnati II | W | 5-1 |
| USA MLS Next Pro League | 2023/08/13 23:00 | Columbus Crew II v New York Red Bulls II | L | 0-5 |
| USA MLS Next Pro League | 2023/08/09 23:00 | Huntsville City v Columbus Crew II | D | 1-1 |
| USA MLS Next Pro League | 2023/08/03 23:00 | Columbus Crew II v Toronto FC II | W | 4-0 |
| USA MLS Next Pro League | 2023/07/28 23:00 | Atlanta United II v Columbus Crew II | W | 0-2 |
| USA MLS Next Pro League | 2023/07/25 16:30 | Columbus Crew II v Philadelphia Union II | L | 2-6 |
| USA MLS Next Pro League | 2023/07/07 23:00 | Toronto FC II v Columbus Crew II | W | 2-3 |
| USA MLS Next Pro League | 2023/07/03 00:35 | Chicago Fire II v Columbus Crew II | L | 2-0 |