 |
 |
| 1st(1st leg) | Waterhouse FC | - | Tivoli Gardens | 1:1 | ||
| 2nd (2nd leg) | Tivoli Gardens | - | Waterhouse FC | 0:2 | ||
| 1st(1st leg): 22/04/2024 23:00 | 2nd (2nd leg): 30/04/2024 02:00 | Winner: Waterhouse FC | ||||
| 1st(1st leg) | Arnett Gardens | - | Portmore United | 1:1 | ||
| 2nd (2nd leg) | Portmore United | - | Arnett Gardens | 0:1 | ||
| 1st(1st leg): 23/04/2024 01:30 | 2nd (2nd leg): 29/04/2024 23:00 | Winner: Arnett Gardens | ||||
