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Molynes United avenged their first-round defeat to Humble Lion with a 2-1 victory on Monday at the Drewsland Mini Stadium, climbing two places to ninth in the points standings.
Rushawn Livingston's 88th-minute goal proved decisive, breaking the tie and securing the win for Molynes United.
The result ended Molynes’ three-game winless streak.
The match spoiled the debut of Alex Thomas as Humble Lion's new head coach.
The Clarendon-based club remains at the bottom of the Wray & Nephew Jamaica Premier League table with 14 points.