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