The 2009 Trinidad and Tobago Classic was the fifth season of the TOYOTA Classic, which is a knockout tournament competition for teams in the TT Pro League and the National Super League. The tournament took place at the conclusion of the 2009 season. San Juan Jabloteh entered as the tournament's defending champion. The tournament commenced on 30 October, with 16 teams competing in single elimination matches.
Qualification
Every club from the TT Pro League automatically qualified for the competition except for Tobago United who did not enter. In addition, following the conclusion of the National Super League season, the top six teams ranked according to the league table qualified. All teams entered the competition at the first round.
The draw for the first round for the fifth edition of the tournament was conducted by Pro LeagueCEO Dexter Skeene on 28 October 2009, at the TOYOTATrinidad and Tobago Limited Barataria showroom. The 16 teams in the competition, valued at TT$50,000 in total sponsorship, were drawn into four groups. All clubs were seeded based on their positions in their respective leagues.
All matches were played over two 45 minutes halves, and in the process if the match were drawn at the end of regulation time, penalty kicks determined the winner.