| 22 Oct 23 | r01        | Mount Pleasant FAMount Pleasan | 1 - 0 | Portmore UnitedPortmore Unit |
| |
| 12 Nov 23 | r04        | DunbeholdenDunbeholden | 0 - 2 | Portmore UnitedPortmore Unit |
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| 19 Nov 23 | r05        | Portmore UnitedPortmore Unit | 2 - 0 | Molynes UnitedMolynes Unite |
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| 22 Nov 23 | r06        | Harbour ViewHarbour View | 1 - 1 | Portmore UnitedPortmore Unit |
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| 28 Nov 23 | r07        | Portmore UnitedPortmore Unit | 0 - 0 | Tivoli GardensTivoli Garden |
| |
| 03 Dec 23 | r08        | Montego Bay UnitedMontego Bay U | 3 - 2 | Portmore UnitedPortmore Unit |
| |
| 10 Dec 23 | r09        | Waterhouse FCWaterhouse FC | 1 - 1 | Portmore UnitedPortmore Unit |
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| 17 Dec 23 | r10        | Portmore UnitedPortmore Unit | 1 - 0 | CavalierCavalier |
| |
| 27 Dec 23 | r11        | Vere UnitedVere United | 0 - 1 | Portmore UnitedPortmore Unit |
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| 31 Dec 23 | r12        | Portmore UnitedPortmore Unit | 2 - 0 | Arnett GardensArnett Garden |
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| 03 Jan 24 | r13        | Humble LionsHumble Lions | 1 - 4 | Portmore UnitedPortmore Unit |
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| 17 Jan 24 | r14        | Portmore UnitedPortmore Unit | 1 - 1 | Mount Pleasant FAMount Pleasan |
| |
| 04 Feb 24 | r17        | Portmore UnitedPortmore Unit | 1 - 1 | DunbeholdenDunbeholden |
| |
| 11 Feb 24 | r18        | Molynes UnitedMolynes Unite | 2 - 2 | Portmore UnitedPortmore Unit |
| |
| 18 Feb 24 | r19        | Portmore UnitedPortmore Unit | 1 - 0 | Harbour ViewHarbour View |
| |
| 25 Feb 24 | r20        | Tivoli GardensTivoli Garden | 0 - 0 | Portmore UnitedPortmore Unit |
| |
| 03 Mar 24 | r21        | Portmore UnitedPortmore Unit | 1 - 1 | Montego Bay UnitedMontego Bay U |
| |
| 10 Mar 24 | r22        | Portmore UnitedPortmore Unit | 0 - 0 | Waterhouse FCWaterhouse FC |
| |
| 18 Mar 24 | r23        | CavalierCavalier | 0 - 1 | Portmore UnitedPortmore Unit |
| |
| 24 Mar 24 | r24        | Portmore UnitedPortmore Unit | 0 - 1 | Vere UnitedVere United |
| |
| 31 Mar 24 | r25        | Arnett GardensArnett Garden | 1 - 1 | Portmore UnitedPortmore Unit |
| |
| 07 Apr 24 | r26        | Portmore UnitedPortmore Unit | 2 - 0 | Humble LionsHumble Lions |
| |
| 23 Apr 24 | r00        | Arnett GardensArnett Garden | 1 - 1 | Portmore UnitedPortmore Unit |
| 29 Apr 24 | r00        | Portmore UnitedPortmore Unit | 0 - 1 | Arnett GardensArnett Garden |