Windward's 1st division travelled to Trent's, St. James to play Maple on Saturday April 20th, but due to heavy rains experienced on the west of the island that afternoon, the game was declared a No Decision without a ball being bowled, giving both teams 2 points. Sunday, Windward travelled to Beckles Road to face last years T20 Cup finalist, YMPC. Winning the toss, captain Rico Wiggins invited the home team to bat first, with openers Dwayne Smith and Raymond Kellman taking their mark at the crease. Kellman's wicket was first to fall at the end of the opening over having not being able to get off the mark against the bowling of Jonathan Griffith, and bringing Kemal Smith to the middle. K. Smith would lose his wicket at the start of the seventh over when he was caught by Shakeem Blades off the bowling of Rashoun Archer, bringing Jai Clarke to join former West Indies cricketer, Dwayne Smith at the crease. Blades would also catch D. Smith, this time off the bowling of Adjani Watkins the following over, the score just 64/3 after after 9 overs. Archer would strike again in the middle of the tenth over, when Jafari Toppin took his second catch of the innings, sending Clarke back to the pavilion and bringing Kemar Smith in to bat. YMPC's next wicket was a result of a run out when Jonathan Griffith threw the ball at the bowlers end to get the wicket of Edwin Currency-Barnett. Ramon Simmonds was dismissed shortly after, having being caught by Wiggins off the bowling of Matthew Alleyne, the score now 135/8 at the end of the sixteenth over. Alleyne would take another wicket during the innings, while Watkins and Archer would both take 3 wickets a piece. YMPC ending their innings with 144 all out. When play resumed Kastun Stoute and Jafari Toppin would open the batting for Windward, and would put up a score of 86 runs when Toppin was bowled by Kemar Smith in the ninth over, having made 51 runs off 32 balls, bringing Wiggins to join Stoute. Wiggins, Latrell Greenidge and Cherran Thompson would all lose their wickets in quick succession, adding 26 runs to the board which was now showing 112/4 with 7 overs remaining. Shakeem Blades would join Stoute in the middle, and the pair carried the score to 145/4 in 16.3 overs, Stoute ending the day with 62 not out off 46 balls, while Blades was 20 not out off 15 balls. Unfortunately Maple won their final match against Lords, giving them 18 points, 4 points ahead of Windward at the end of the preliminary round of the tournament. Windward's next match is June 1st when they travel to Dayrells Road to play Wanderers in round one of the Super Cup Competition.