| United Premier Soccer League | 01/09 20:30 | - | PSE Conquistadores v Winter Haven United FC | W | 2-3 | |
| United Premier Soccer League | 09/09 15:01 | - | Huracan FC v Winter Haven United FC | D | 0-0 | |
| United Premier Soccer League | 09/02 00:08 | - | America SC v Winter Haven United FC | L | 7-1 |