Chasing a modest 112 for victory, the Leewards crumbled in the middle of their innings, and could not recover to challenge the Windwards' total.
The loss ensured the Leewards remained at the bottom of the standings with zero points from four matches, and just two matches to play in St Lucia to complete their campaign.
The Windwards, led by West Indies skipper Darren Sammy, moved onto eight points from three matches with two wins and one loss.
When the Windwards won the toss and elected to bat first, they seemed to be on course for a big total with Andre Fletcher smashing a six and a four in his 25-ball 24.
But Fletcher could not get the ball over the ropes in the middle overs and was eventually bowled by pacer Gavin Tonge with the score on 50 for three in the tenth over.
Miles Bascombe, who celebrated his 27th birthday yesterday, top-scored with 29 off 31 balls, hitting two fours and a six before he was caught by Kieran Powell off Anthony Martin in the final over.
But the total proved to be out of the reach of the Leewards, who had taken Jamaica to the brink of defeat a day before.
They were off to a promising start, but lost the plot as soon as the run rate started climbing.
Powell was expected to help them to their target, but he could only manage 16 off 24 balls with two fours.
He was the first Leewards wicket to fall, caught off the bowling of Johnson in the seventh over of the chase with the score on 33.
They were still on course for the win, but spinner Liam Sebastien (four for 17) set them back taking two wickets off consecutive balls in the 16th over to send back Devon Thomas for 20 and danger man Rahkeem Cornwall, both batsmen being bowled with the score on 64.
Thomas was striking the ball well, pulling Sebastien over square led for a six off the spinner previous over.
Thomas looked like the one to take them all the way after pulling Garey Mathurin to the mid-wicket fence, but Sebastien eventually got his man, rattling the stumps of the right-handed wicket-keeper.
Justin Athanaze kept the Leewards in the fight with 24 off 15 with two sixes, one off Darren Sammy and one of Shane Shillingford, at the end of the innings but with 21 needed in the final over, it was always going to be a difficult task.
Athanaze was eventually run out in the final over to end the Leewards' resistance.
By the end of the match, the crowd had built up from hundreds to thousands and they were just warming up for the big clash between defending champions Trinidad and Tobago and 2010 winners Guyana which bowled off at 8 p.m. last night.