[1] Similar to the FA Trophy, it is played on a knockout (single elimination) basis in September and October towards the beginning of each Pro League season.

[3] The competition began in 2000, under the name of the League Cup, with San Juan Jabloteh winning the inaugural tournament by defeating Defence Force 1–0 at Marvin Lee Stadium.

[6] The Eastern Lions exacted revenge by defeating Defence Force 3–0 on penalties after the match ended 1–1 the following year in 2010 to claim their first league cup title.

[7][8] The competition is open to all clubs of the TT Pro League and is divided into three rounds consisting of single-legged matches.

During the first ten years of competition, teams were seeded as determined by their league position at the time of the quarterfinal pairings announcement.

Defence Force and Police were unable to compete due to being called into service for increased crime in portions of the country.