In what was supposed to be an intense face-off between Jamaica and Leeward Islands, the semi-final match took an unexpected turn as Leeward Islands emerged victorious with a stunning victory. Similarly, the first semi-final match between Barbados and Trinidad & Tobago at Tarouba also ended in a surprising upset, with Barbados coming out on top. Furthermore, Combined Campuses and Colleges faced defeat by Leeward Islands in their 27th match of the Super50 Cup, adding to the series of unexpected outcomes in the tournament.