| saturday december 28 - 16:15 |  FC Greenland #3 | 0-2 | 0 | League of Barbados [2] | SF | | |
| friday december 27 - 10:37 | FC Bridgetown #23 | 0-0 | 1 | League of Barbados [2] | SF | | |
| thursday december 26 - 01:40 | FC Speightstown #7 | 1-0 | 0 | League of Barbados [2] | SF | | |
| monday december 23 - 13:48 | FC Bridgetown #18 | 1-0 | 0 | League of Barbados [2] | SF | | |
| sunday december 22 - 16:51 | FC Bridgetown #24 | 0-0 | 1 | League of Barbados [2] | SF | | |
| saturday december 21 - 19:19 | FC Blackmans | 0-0 | 1 | League of Barbados [2] | SM | | |
| friday december 20 - 16:50 | Barbados Wings | 0-1 | 0 | League of Barbados [2] | SM | | |
| tuesday december 17 - 16:18 | FC Bridgetown #23 | 0-0 | 1 | League of Barbados [2] | SF | | |
| monday december 16 - 16:43 | FC Speightstown #7 | 1-0 | 3 | League of Barbados [2] | SM | | |
| saturday december 14 - 16:48 | FC Crab Hill | 1-0 | 3 | League of Barbados [2] | RF | | |
| friday december 13 - 15:46 | FC Greenland #3 | 0-0(5-3) | 1 | Cup | SF | | |
| thursday december 5 - 12:26 | FC Bridgetown #8 | 3-4* | 3 | Cup | SF | | |
