Two pre-season friendlies were announced by Professional Football Jamaica Limited (PFJL) prior to the start of the 2023–24 season.

[4] While Mount Pleasant defeated Cavalier 3–1 in the Powerade Finals rematch held at the Drax Hall Sports Complex, there were uncertainties whether the Boom El Classico match would be allowed to be hosted at the Anthony Spaulding Sports Complex due to curfews in the surrounding areas.

[6][7] Arnett Gardens defeated Waterhouse 2–0 to retain the Boom El Classico trophy after also running out winners in the inaugural edition held in the 2022 preseason.

Cavalier and Harbour View match week one and two fixtures were postponed due to both teams involvement in the knockout stage of the 2023 CONCACAF Caribbean Cup.

In a late announcement by the PFJL, all 5 match week two fixtures on Sunday, 29 October 2023, were postponed due to Reggae Girls hosting Guatemala at home in the 2024 CONCACAF W Gold Cup qualification competition.

[10][11] Newly promoted premier league club Lime Hall parted ways with head coach David Pryce on November 20.

Thomas parted ways with Molynes on November 29 after a run of 4 consecutive losses, leaving the club sitting at the bottom of the table and winless after 7 match weeks.

Justin Dunn netted all 3 goals for Tivoli Gardens to earn the premier league's first hat-trick of season, he was rewarded with the man of the match award for his outstanding derby performance.

Despite being reduced to 10 men, Tivoli Gardens maintained their relentless pressure and were rewarded with a penalty in the 73rd minute, expertly converted by striker Justin Dunn, bringing his season tally to 10 goals.

Undeterred, Tivoli Gardens continued to press forward and eventually took the lead in the 76th minute through a goal by substitute Steven Clarke.