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.

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 League CEO Dexter Skeene on 28 October 2009, at the TOYOTA Trinidad 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.

St. Ann's Rangers, San Juan Jabloteh, Defence Force, and Joe Public were drawn as the top seeds in Groups A, B, C, and D, respectively.

The following clubs have qualified for this year's edition of the TOYOTA Classic:

The schedule for the 2009 TOYOTA Classic, as announced by the TT Pro League and National Super League:

...
Wikipedia