The 2008 Trinidad and Tobago Pro Bowl was the fifth season of the CourtsPro Bowl, which is a knockout tournament competition for teams in the TT Pro League. W Connection entered as the tournament's defending champion.[1] The tournament commenced on 6 May, with 10 teams competing in single elimination matches and concluded on 23 May, with Caledonia AIA defeating Defence Force 2–0 to claim the title.
Qualification
Every club from the TT Pro League automatically qualified for the competition. Seeding was determined by the league standings following the fourth match day of the 2008 season. Teams ranked seventh to tenth were placed directly into the qualifying round which determined the seventh and eight spots in the quarterfinals.
All matches were played for 90 minutes duration, at the end of which if the match was still tied, penalty-kicks were used to determine the match winner.