The season began on 14 October 2018 and ended on 17 February 2019.
[1] For the first time, teams from the two main islands, Saint Croix and Saint Thomas, competed together in the same league (previously, they played in their own leagues in St. Croix and St. Thomas respectively before the top teams of the two leagues advanced to the playoffs).
The top four teams, regardless of island, advanced to the playoffs.
Helenites, who play at the 1,000-capacity Grove Place Park, won championship qualified for Caribbean Club Shield.
This article about a CONCACAF/North, Central American and Caribbean association football competition is a stub.