18/05 - 12:30
18/05 - 14:30
18/05 - 14:30
18/05 - 15:00
18/05 - 15:00
18/05 - 16:15
18/05 - 17:00
18/05 - 19:45
18/05 - 20:00
19/05 - 11:30
18/05 - 12:30
18/05 - 14:30
18/05 - 14:30
18/05 - 15:00
18/05 - 15:00
18/05 - 16:15
18/05 - 17:00
18/05 - 19:45
18/05 - 20:00
19/05 - 11:30
18/05 - 17:00
18/05 - 19:45
19/05 - 11:30
18/05 - 14:30
18/05 - 14:30
| 2023-12-07 00:00 | F | Cavalier SC |  | 0-2 |  | SV Robinhood | Franklin Singodikromo 89', Jamilhio Rigters 90' | |
| 2023-11-18 15:30 | QF | Jamaica |  | 1-2 |  | Canada | Shamar Nicholson 56'; Jonathan David 45', Stephen Eustaquio 85' | |
| 2023-09-28 01:00 | Grp.B | Harbour View |  | 3-2 | | SV Robinhood | Omar Thompson 45', Shaqueil Bradford 55' 69'; Shaquille Cairo 33', Jamilhio Rigters 50' (pen.) | |
| 2023-09-22 01:00 | Grp.B | Dunbeholden |  | 0-2 | | SV Robinhood | Shaquille Cairo 15' 55' | |
| 2023-09-13 01:00 | Grp.B | Jamaica | | 2-2 |  | Haiti | Bobby Reid 83' (pen.); Louicius Deedson 11' 14', Ricardo Ade 51' (o.g.) | |
| 2023-09-09 02:10 | Grp.B | Jamaica | | 1-0 |  | Honduras | Demarai Gray 64' |
