| 22 Oct 23 | r01        | Tivoli GardensTivoli Garden | 3 - 0 | Waterhouse FCWaterhouse FC |
| |
| 06 Nov 23 | r03        | Tivoli GardensTivoli Garden | 1 - 2 | Vere UnitedVere United |
| |
| 12 Nov 23 | r04        | Arnett GardensArnett Garden | 1 - 3 | Tivoli GardensTivoli Garden |
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| 20 Nov 23 | r05        | Tivoli GardensTivoli Garden | 4 - 1 | Humble LionsHumble Lions |
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| 23 Nov 23 | r06        | Tivoli GardensTivoli Garden | 0 - 1 | Mount Pleasant FAMount Pleasan |
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| 28 Nov 23 | r07        | Portmore UnitedPortmore Unit | 0 - 0 | Tivoli GardensTivoli Garden |
| |
| 10 Dec 23 | r09        | DunbeholdenDunbeholden | 2 - 2 | Tivoli GardensTivoli Garden |
| |
| 17 Dec 23 | r10        | Tivoli GardensTivoli Garden | 1 - 0 | Molynes UnitedMolynes Unite |
| |
| 21 Dec 23 | r02        | CavalierCavalier | 1 - 1 | Tivoli GardensTivoli Garden |
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| 27 Dec 23 | r11        | Harbour ViewHarbour View | 0 - 3 | Tivoli GardensTivoli Garden |
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| 03 Jan 24 | r13        | Tivoli GardensTivoli Garden | 1 - 2 | Montego Bay UnitedMontego Bay U |
| |
| 17 Jan 24 | r14        | Waterhouse FCWaterhouse FC | 0 - 1 | Tivoli GardensTivoli Garden |
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| 22 Jan 24 | r15        | Tivoli GardensTivoli Garden | 0 - 0 | CavalierCavalier |
| |
| 29 Jan 24 | r16        | Vere UnitedVere United | 1 - 2 | Tivoli GardensTivoli Garden |
| |
| 06 Feb 24 | r17        | Tivoli GardensTivoli Garden | 3 - 1 | Arnett GardensArnett Garden |
| |
| 11 Feb 24 | r18        | Humble LionsHumble Lions | 0 - 2 | Tivoli GardensTivoli Garden |
| |
| 18 Feb 24 | r19        | Mount Pleasant FAMount Pleasan | 1 - 0 | Tivoli GardensTivoli Garden |
| |
| 25 Feb 24 | r20        | Tivoli GardensTivoli Garden | 0 - 0 | Portmore UnitedPortmore Unit |
| |
| 10 Mar 24 | r22        | Tivoli GardensTivoli Garden | 1 - 1 | DunbeholdenDunbeholden |
| |
| 20 Mar 24 | r23        | Molynes UnitedMolynes Unite | 3 - 6 | Tivoli GardensTivoli Garden |
| |
| 26 Mar 24 | r24        | Tivoli GardensTivoli Garden | 1 - 0 | Harbour ViewHarbour View |
| |
| 07 Apr 24 | r26        | Montego Bay UnitedMontego Bay U | 2 - 1 | Tivoli GardensTivoli Garden |
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| 22 Apr 24 | r00        | Waterhouse FCWaterhouse FC | 1 - 1 | Tivoli GardensTivoli Garden |
| 30 Apr 24 | r00        | Tivoli GardensTivoli Garden | 0 - 2 | Waterhouse FCWaterhouse FC |