| VS - UPSL | 01/10 22:30 | - | Diaspora United v Orlando City SS HC | L | 4-2 | |
| VS - UPSL | 11/30 00:30 | - | Orlando City SS HC v FK Orlando | L | 1-2 | |
| VS - UPSL | 11/16 00:30 | - | Orlando City HC v OFC Barca | L | 0-1 | |
| VS - UPSL | 11/01 00:12 | - | Deportivo Lake Mary v Orlando City HC | L | 3-0 | |
| VS - UPSL | 10/18 23:46 | - | Deportivo Lake Mary v Orlando City SS HC | L | 2-1 | |
| VS - UPSL | 10/17 23:30 | - | GOSA Spurs v Orlando City HC | D | 2-2 | |
| VS - UPSL | 10/10 23:53 | - | Inter Orlando FC v Orlando City HC | W | 1-3 | |
| VS - UPSL | 10/04 21:00 | - | Inter Orlando FC v Orlando City SS HC | D | 2-2 |