[5] Orlando City SC II 3-2 New York Red Bulls II [4] 2023-05-29 23:00
Stadium: Osceola County Stadium Round: 1
Head to Head
| USA USL Championship | 2017/10/07 23:30 | Orlando City II v New York Red Bulls II | L | 5-6 |
| USA USL Championship | 2017/04/14 23:00 | New York Red Bulls II v Orlando City II | L | 3-1 |
| USA USL Championship | 2016/10/02 20:00 | New York Red Bulls II v Orlando City II | L | 4-0 |
| USA USL Championship | 2016/08/12 23:00 | New York Red Bulls II v Orlando City II | L | 5-1 |
| USA USL Championship | 2016/06/19 23:30 | Orlando City II v New York Red Bulls II | D | 2-2 |
Home History
| 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 | D | 2-2 |
| 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 II | W | 3-2 |
| USA MLS Next Pro League | 2023/04/23 23:00 | Orlando City II v New York City FC II | W | 10-9 |
| USA MLS Next Pro League | 2023/04/16 23:30 | Atlanta United II v Orlando City II | L | 3-1 |
| USA MLS Next Pro League | 2023/04/09 22:00 | Orlando City II v Inter Miami CF II | W | 2-0 |
Away History
| USA MLS Next Pro League | 2023/05/27 00:00 | Huntsville City v New York Red Bulls II | W | 1-2 |
| USA MLS Next Pro League | 2023/05/21 23:00 | New York Red Bulls II v Inter Miami CF II | W | 1-0 |
| USA MLS Next Pro League | 2023/05/14 23:00 | New York Red Bulls II v New York City FC II | W | 2-0 |
| USA MLS Next Pro League | 2023/05/07 23:00 | New York Red Bulls II v Philadelphia Union II | L | 1-2 |
| USA MLS Next Pro League | 2023/04/30 22:00 | Chicago Fire II v New York Red Bulls II | W | 0-3 |
| USA MLS Next Pro League | 2023/04/21 23:00 | New England Revolution II v New York Red Bulls II | W | 0-1 |
| USA MLS Next Pro League | 2023/04/16 23:00 | New York Red Bulls II v Huntsville City | W | 1-0 |
| USA MLS Next Pro League | 2023/04/09 23:00 | New York Red Bulls II v Crown Legacy | L | 1-3 |