[1] W Connection entered as the defending champions after having defeated Caledonia AIA 2–0 in the 2007 final for their fourth consecutive league cup title.
The automatic quarterfinal qualifiers in order of league position were: San Juan Jabloteh, W Connection, Caledonia AIA, United Petrotrin, Joe Public, and St. Ann's Rangers.
The knockout cup began in the qualifying round with Tobago United and Defence Force recording upsets over higher-seeded Ma Pau and North East Stars respectively.
Before the final match, St. Ann's Rangers used strikes from Keyon Edwards and Josimar Belgrave in two minutes to put away top seeded San Juan Jabloteh for a third-place finish.
After being dead-locked 2–2 at the end of regulation, W Connection used a miss by Joe Public's Jason Springer on the twelfth kick from the penalty spot to win 6–5 in the shootout.