Concacaf Caribbean Cup
Caribbean Cup 
| 23-Aug-23 18:00 | 23Aug | Group B | Harbour V | 1:0 | DFC | Pennyfeather |
| 24-Aug-23 20:00 | 24Aug | Group A | Defence | 1:1 | Cavalier | Greene |
| 24-Aug-23 20:00 | 24Aug | Group B | Cibao | 1:1 | Pantoja | Radix |
| 25-Aug-23 10:00 | 25Aug | Group A | Moca | 1:0 | AC PoS | Dewar |
| 30-Aug-23 18:00 | 30Aug | Group A | Gold Lion | 0:1 | Defence | da Silva, N |
| 30-Aug-23 20:00 | 30Aug | Group B | Pantoja | 1:1 | DFC | Gumbs |
| 31-Aug-23 18:00 | 31Aug | Group A | Cavalier | 2:1 | AC PoS | Martinez, Yadel |
| 31-Aug-23 20:00 | 31Aug | Group B | Robinhood | 1:0 | Cibao | Ward, K |
| 19-Sep-23 20:00 | 19Sep | Group A | Cavalier | 3:0 | Moca | Radix |
| 20-Sep-23 18:00 | 20Sep | Group A | AC PoS | 2:3 | Gold Lion | Carrasco |
| 20-Sep-23 20:00 | 20Sep | Group B | Pantoja | 1:1 | Harbour V | Culley |
| 21-Sep-23 20:00 | 21Sep | Group B | DFC | 0:2 | Robinhood | Gaymes |
| 26-Sep-23 20:00 | 26Sep | Group A | Moca | 3:0 | Gold Lion | Elie |
| 27-Sep-23 20:00 | 27Sep | Group B | Harbour V | 3:2 | Robinhood | Williams, K |
| 28-Sep-23 18:00 | 28Sep | Group A | AC PoS | 1:1 | Defence | Ward, K |
| 28-Sep-23 20:00 | 28Sep | Group B | DFC | 2:1 | Cibao | Gumbs |
| 04-Oct-23 20:00 | 04Oct | Group A | Gold Lion | 2:5 | Cavalier | Pennyfeather |
| 04-Oct-23 20:00 | 04Oct | Group A | Defence | 0:2 | Moca | Greene |
| 05-Oct-23 20:00 | 05Oct | Group B | Robinhood | 3:1 | Pantoja | de Leça |
| 05-Oct-23 20:00 | 05Oct | Group B | Cibao | 2:1 | Harbour V | Martinez, Yadel |
Matchday 6 - Semi-finals | ||||||
| 24-Oct-23 19:00 | 24Oct | Semi-finals | Harbour V | 0:5 | Cavalier | Martinez, Yadel |
| 25-Oct-23 18:00 | 25Oct | Semi-finals | Moca | 1:0 | Robinhood | Ward, K |
Matchday 7 - Semi-finals | ||||||
| 31-Oct-23 19:00 | 31Oct | Semi-finals | Cavalier | 0:0 | Harbour V | Greene |
| 02-Nov-23 21:00 | 02Nov | Semi-finals | Robinhood | 1:0 | Moca | Radix |
Matchday 8 - 3rd place play-offs | ||||||
| 28-Nov-23 18:00 | 28Nov | 3rd place play-offs | Harbour V | 1:2 | Moca | de Leça |
| 30-Nov-23 18:00 | 30Nov | Finals | Robinhood | 1:0 | Cavalier | Carrasco |
Matchday 9 - 3rd place play-offs | ||||||
| 05-Dec-23 19:00 | 05Dec | 3rd place play-offs | Moca | 1:1 | Harbour V | da Silva, N |
| 06-Dec-23 19:00 | 06Dec | Finals | Cavalier | 0:2 | Robinhood | Williams, K |