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| | | | 23-Aug-23 - Matchday 1 | Group B | Harbour V | 1-0 | DFC | |  Pennyfeather | | 24-Aug-23 | Group A | Defence | 1-1 | Cavalier | |  Greene | | 24-Aug-23 | Group B | Cibao | 1-1 | Pantoja | |  Radix | | 25-Aug-23 | Group A | Moca | 1-0 | AC PoS | |  Dewar | | | | | 30-Aug-23 - Matchday 2 | Group A | Gold Lion | 0-1 | Defence | |  da Silva, N | | 30-Aug-23 | Group B | Pantoja | 1-1 | DFC | |  Gumbs | | 31-Aug-23 | Group A | Cavalier | 2-1 | AC PoS | |  Martinez, Yadel | | 31-Aug-23 | Group B | Robinhood | 1-0 | Cibao | | Ward, K | | | | | 19-Sep-23 - Matchday 3 | Group A | Cavalier | 3-0 | Moca | | Radix | | 20-Sep-23 | Group A | AC PoS | 2-3 | Gold Lion | |  Carrasco | | 20-Sep-23 | Group B | Pantoja | 1-1 | Harbour V | | Culley | | 21-Sep-23 | Group B | DFC | 0-2 | Robinhood | |  Gaymes | | | | | 26-Sep-23 - Matchday 4 | Group A | Moca | 3-0 | Gold Lion | |  Elie | | 27-Sep-23 | Group B | Harbour V | 3-2 | Robinhood | |  Williams, K | | 28-Sep-23 | Group A | AC PoS | 1-1 | Defence | | Ward, K | | 28-Sep-23 | Group B | DFC | 2-1 | Cibao | | Gumbs | | | | | 04-Oct-23 - Matchday 5 | Group A | Gold Lion | 2-5 | Cavalier | | Pennyfeather | | 04-Oct-23 | Group A | Defence | 0-2 | Moca | | Greene | | 05-Oct-23 | Group B | Robinhood | 3-1 | Pantoja | |  de Leça | | 05-Oct-23 | Group B | Cibao | 2-1 | Harbour V | | Martinez, Yadel | | | | | 24-Oct-23 - Matchday 6 | Semi-finals | Harbour V | 0-5 | Cavalier | | Martinez, Yadel | | 25-Oct-23 | Semi-finals | Moca | 1-0 | Robinhood | | Ward, K | | | | | 31-Oct-23 - Matchday 7 | Semi-finals | Cavalier | 0-0 | Harbour V | | Greene | | 02-Nov-23 | Semi-finals | Robinhood | 1-0
(3-2) | Moca | | Radix | | | | | 28-Nov-23 - Matchday 8 | 3rd place play-offs | Harbour V | 1-2 | Moca | | de Leça | | 30-Nov-23 | Finals | Robinhood | 1-0 | Cavalier | | Carrasco | | | | | 05-Dec-23 - Matchday 9 | 3rd place play-offs | Moca | 1-1 | Harbour V | | da Silva, N | | 06-Dec-23 | Finals | Cavalier | 0-2 | Robinhood | | Williams, K | |
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