[3] In May 2021, the Jamaican Football Federation announced that the Jamaica Premier League would resume, playing a shortened season between June and September, competed by the 12 teams from the previous season[4] In June 2021, UWI F.C.

announced it would withdraw ahead of the 2021 season due to the modified schedule conflicting with other player commitments; leaving 11 teams in the competition.

The 2021 season will operate under a modified compressed schedule where each team will play each other once during the preliminary round of the competition.

For the top tier, the top two teams will automatically advance to the semi-finals, while the other four teams will play for the remaining semi-finals spots.

Cavalier progresses 1-0 on aggregate Waterhouse progresses 2-1 on aggregates Tivoli Gardens won 1-1(4-3 on penalties) Cavalier won 1-1(5-4 on penalties)