| 23 Oct 22 | r01        | Portmore UnitedPortmore Unit | 1 - 1 | Montego Bay UnitedMontego Bay U |
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| 08 Nov 22 | r03        | Portmore UnitedPortmore Unit | 0 - 0 | Vere UnitedVere United |
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| 17 Nov 22 | r02        | Arnett GardensArnett Garden | 1 - 1 | Portmore UnitedPortmore Unit |
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| 22 Nov 22 | r05        | Mount Pleasant FAMount Pleasan | 0 - 0 | Portmore UnitedPortmore Unit |
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| 04 Dec 22 | r04        | Chapelton MaroonsChapelton Mar | 0 - 1 | Portmore UnitedPortmore Unit |
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| 20 Dec 22 | r06        | Portmore UnitedPortmore Unit | 0 - 0 | DunbeholdenDunbeholden |
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| 28 Dec 22 | r07        | FaulklandFaulkland | 1 - 3 | Portmore UnitedPortmore Unit |
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| 03 Jan 23 | r08        | Portmore UnitedPortmore Unit | 1 - 0 | Harbour ViewHarbour View |
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| 08 Jan 23 | r09        | Tivoli GardensTivoli Garden | 0 - 0 | Portmore UnitedPortmore Unit |
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| 15 Jan 23 | r10        | Portmore UnitedPortmore Unit | 1 - 2 | CavalierCavalier |
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| 22 Jan 23 | r11        | Humble LionsHumble Lions | 1 - 0 | Portmore UnitedPortmore Unit |
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| 29 Jan 23 | r12        | Waterhouse FCWaterhouse FC | 1 - 1 | Portmore UnitedPortmore Unit |
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| 06 Feb 23 | r13        | Portmore UnitedPortmore Unit | 1 - 1 | Molynes UnitedMolynes Unite |
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| 12 Feb 23 | r14        | Montego Bay UnitedMontego Bay U | 1 - 1 | Portmore UnitedPortmore Unit |
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| 19 Feb 23 | r15        | Portmore UnitedPortmore Unit | 1 - 2 | Arnett GardensArnett Garden |
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| 26 Feb 23 | r16        | Vere UnitedVere United | 0 - 2 | Portmore UnitedPortmore Unit |
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| 06 Mar 23 | r17        | Portmore UnitedPortmore Unit | 0 - 0 | Chapelton MaroonsChapelton Mar |
| |
| 19 Mar 23 | r19        | DunbeholdenDunbeholden | 1 - 3 | Portmore UnitedPortmore Unit |
| |
| 26 Mar 23 | r20        | Portmore UnitedPortmore Unit | 4 - 0 | FaulklandFaulkland |
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| 02 Apr 23 | r21        | Harbour ViewHarbour View | 0 - 1 | Portmore UnitedPortmore Unit |
| |
| 06 Apr 23 | r18        | Portmore UnitedPortmore Unit | 0 - 0 | Mount Pleasant FAMount Pleasan |
| |
| 09 Apr 23 | r22        | Portmore UnitedPortmore Unit | 2 - 1 | Tivoli GardensTivoli Garden |
| |
| 16 Apr 23 | r23        | CavalierCavalier | 2 - 0 | Portmore UnitedPortmore Unit |
| |
| 23 Apr 23 | r24        | Portmore UnitedPortmore Unit | 1 - 1 | Humble LionsHumble Lions |
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| 30 Apr 23 | r25        | Portmore UnitedPortmore Unit | 1 - 1 | Waterhouse FCWaterhouse FC |
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| 07 May 23 | r26        | Molynes UnitedMolynes Unite | 0 - 3 | Portmore UnitedPortmore Unit |