| 05 Nov 23 | r03        | Humble LionsHumble Lions | 1 - 1 | Molynes UnitedMolynes Unite |
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| 13 Nov 23 | r04        | Harbour ViewHarbour View | 2 - 2 | Humble LionsHumble Lions |
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| 20 Nov 23 | r05        | Tivoli GardensTivoli Garden | 4 - 1 | Humble LionsHumble Lions |
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| 23 Nov 23 | r06        | Humble LionsHumble Lions | 3 - 2 | Montego Bay UnitedMontego Bay U |
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| 27 Nov 23 | r07        | Waterhouse FCWaterhouse FC | 0 - 1 | Humble LionsHumble Lions |
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| 10 Dec 23 | r09        | Vere UnitedVere United | 2 - 1 | Humble LionsHumble Lions |
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| 17 Dec 23 | r10        | Humble LionsHumble Lions | 0 - 2 | Arnett GardensArnett Garden |
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| 21 Dec 23 | r02        | DunbeholdenDunbeholden | 1 - 0 | Humble LionsHumble Lions |
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| 31 Dec 23 | r12        | Mount Pleasant FAMount Pleasan | 1 - 0 | Humble LionsHumble Lions |
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| 03 Jan 24 | r13        | Humble LionsHumble Lions | 1 - 4 | Portmore UnitedPortmore Unit |
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| 10 Jan 24 | r08        | Humble LionsHumble Lions | 1 - 2 | CavalierCavalier |
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| 21 Jan 24 | r15        | Humble LionsHumble Lions | 0 - 0 | DunbeholdenDunbeholden |
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| 28 Jan 24 | r16        | Molynes UnitedMolynes Unite | 3 - 2 | Humble LionsHumble Lions |
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| 05 Feb 24 | r17        | Humble LionsHumble Lions | 2 - 4 | Harbour ViewHarbour View |
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| 11 Feb 24 | r18        | Humble LionsHumble Lions | 0 - 2 | Tivoli GardensTivoli Garden |
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| 18 Feb 24 | r19        | Montego Bay UnitedMontego Bay U | 3 - 0 | Humble LionsHumble Lions |
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| 25 Feb 24 | r20        | Humble LionsHumble Lions | 1 - 4 | Waterhouse FCWaterhouse FC |
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| 04 Mar 24 | r21        | CavalierCavalier | 1 - 1 | Humble LionsHumble Lions |
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| 10 Mar 24 | r22        | Humble LionsHumble Lions | 3 - 0 | Vere UnitedVere United |
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| 19 Mar 24 | r23        | Arnett GardensArnett Garden | 5 - 1 | Humble LionsHumble Lions |
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| 31 Mar 24 | r25        | Humble LionsHumble Lions | 0 - 1 | Mount Pleasant FAMount Pleasan |
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| 07 Apr 24 | r26        | Portmore UnitedPortmore Unit | 2 - 0 | Humble LionsHumble Lions |