The 2018–19 Regional Super50 was the 45th edition of the Regional Super50, the domestic limited-overs cricket competition for the countries of the Cricket West Indies (CWI). The tournament started on 3 October 2018. The players' draft for the tournament took place in May 2018. The Windward Islands were the defending champions. On 6 October 2018, Chris Gayle played in his final List A cricket match for Jamaica, scoring a century, with Jamaica beating Barbados by 33 runs. In the final, Combined Campuses and Colleges beat Guyana by six wickets to win their first Regional Super50 title.