| fredag september 1 - 08:24 |  The Baby Red Dragon [0] | 2-0 | Huskies In The Sun [3] |
| fredag september 1 - 11:39 | FC Charlotte Amalie #18 [1] | 1-3 | FC Saint Croix #13 [0] |
| fredag september 1 - 13:51 | FC Saint Croix #22 [0] | 0-1 | Lollapa Losers [3] |
| fredag september 1 - 13:51 | FC Cruz Bay #5 [0] | 3-2 | FC Charlotte Amalie #23 [1] |
| fredag september 1 - 19:42 | FC Charlotte Amalie #11 [3] | 2-1 | FC Coral Bay [1] |
| fredag september 1 - 20:23 | FC Charlotte Amalie #13 [1] | 2-1 | FC Charlotte Amalie #25 [1] |
| fredag september 1 - 20:45 | Cataclysm FC [1] | 1-2 | FC Saint Croix [3] |
