[1] Robinhood defeated title holders Club Franciscain in the final to win their first CONCACAF Caribbean Club Shield, and later defeated Real Hope in a playoff to qualify for the CONCACAF League.

Among the 31 CFU member associations, 27 of them were classified as non-professional leagues and each may enter one team in the CONCACAF Caribbean Club Shield.

A total of 13 teams (from 13 associations) entered the 2019 CONCACAF Caribbean Club Shield.

[2] The matches were played at the Ergilio Hato Stadium and Stadion dr. Antoine Maduro in Willemstad.

The draw for the group stage was held on 11 January 2019, 11:00 EST (UTC−5), at the CONCACAF Headquarters in Miami, United States.