The draw for the first round for the fourth edition of the tournament was conducted by Pro League CEO Dexter Skeene on 26 November 2008, at the Constantine Stand, Queen's Park Oval.
[1] W Connection, Caledonia AIA, San Juan Jabloteh, and Joe Public of the TT Pro League were drawn as the top seeds in Groups A, B, C, and D, respectively.
One week after the quarterfinals, on 12 December, St. Ann's Rangers continued their run through the tournament with a 1–0 win over fellow Pro League side North East Stars.
In the consolation match-up, Caledonia AIA narrowly defeated North East Stars 6–5 on penalty kicks, after the match ended 2–2 in regulation, to claim the competition's third place.
In the final, San Juan Jabloteh claimed their first TOYOTA Classic title with a 2–1 win over St. Ann's Rangers using goals from Jason Marcano and Trent Noel.