2018–19 National Premier League

The 2018–19 Red Stripe Premier League was the 45th season of the National Premier League, the top division football competition in Jamaica. The season began on 16 September 2018 and ended on 29 April 2019. Portmore United were the defending champions, having won their 6th title the previous season.

Teams
Sandals South Coast FC and Boys' Town finished 11th and 12th in last season's competition and were relegated to their respective regional Super Leagues, the Western Super League and KSAFA Super League respectively.

At the end of last season, the champions of the four Super Leagues participated in a promotion playoff double round robin tournament. Dunbeholden F.C. and Mount Pleasant Football Academy finished 1st and 2nd after the playoff and were promoted to the National Premier League for this season.

Quarterfinals
Mount Pleasant F.A. progresses 3-2 on aggregate.

Cavalier progresses 3-0 on aggregate.

Semifinals
The winners of these ties will qualify for the Caribbean Club Championship.

Portmore United progress 3-2 on aggregate.

Waterhouse progresses 3-0 on aggregate.