| monday january 6 - 13:50 |  FC Bridgetown #8 | 1-3 | 3 | League of Barbados [2] | SF | | |
| monday january 6 - 04:02 | FC Bridgetown #22 U21 | 0-6 | 3 | U21 league | LCF |  | |
| sunday january 5 - 13:22 | FC Bridgetown #18 | 1-2 | 3 | League of Barbados [2] | SF | | |
| saturday january 4 - 16:03 | FC Bridgetown #18 U21 | 6-1 | 3 | U21 league | SF | | |
| friday january 3 - 16:05 | FC Bridgetown #22 U21 | 4-0 | 3 | U21 league | LCF | | |
| wednesday january 1 - 16:01 | HOLLANDITIS U21 | 0-4 | 0 | U21 league | LCF | | |
| wednesday january 1 - 01:49 | FC Speightstown #7 | 3-1 | 0 | League of Barbados [2] | SF | | |
| tuesday december 31 - 16:21 | FC Greenland #3 | 1-2 | 0 | League of Barbados [2] | SF | | |
| tuesday december 31 - 16:04 | HOLLANDITIS U21 | 0-5 | 0 | U21 league | LCF | | |
| monday december 30 - 10:30 | FC Bridgetown #23 | 3-2 | 0 | League of Barbados [2] | SF | | |
| sunday december 29 - 16:15 | FC Four Cross Roads | 2-0 | 3 | League of Barbados [2] | SF | | |
| sunday december 29 - 16:04 | FC Worga 1492 U21 | 1-3 | 0 | U21 league | SF | | |
| saturday december 28 - 17:05 | HOLLANDITIS U21 | 4-0 | 0 | U21 league | SF | | |
| saturday december 28 - 14:43 | FC Crab Hill | 1-3 | 3 | League of Barbados [2] | SF | | |
| friday december 27 - 16:18 | FC Bridgetown #8 | 1-1 | 1 | League of Barbados [2] | SF | | |
| thursday december 26 - 16:28 | FC Bridgetown #18 | 2-1 | 3 | League of Barbados [2] | SF | | |
| wednesday december 25 - 22:17 | FC Bridgetown #24 | 1-2 | 3 | League of Barbados [2] | SF | | |
| wednesday december 25 - 16:03 | FC Greenland #4 U21 | 0-2 | 3 | U21 league | SF | | |
| friday december 20 - 16:50 | FC Four Cross Roads | 0-1 | 3 | League of Barbados [2] | SF | | |
| friday december 20 - 13:04 | FC Bridgetown #18 U21 | 0-0 | 1 | U21 league | LCF | | |
| thursday december 19 - 16:05 | FC Worga 1492 U21 | 2-0 | 0 | U21 league | LCF | | |
| wednesday december 18 - 16:36 | FC Crab Hill | 4-1 | 3 | League of Barbados [2] | SF | | |
| tuesday december 17 - 13:27 | FC Bridgetown #8 | 2-0 | 0 | League of Barbados [2] | SF | | |
| monday december 16 - 01:01 | FC Speightstown #7 U21 | 0-4 | 3 | U21 league | S | | |
| sunday december 15 - 12:05 |  Gibraltar #26 U21 | 1-3 | 3 | U21 Youth Cup | RCF | | |
