The 2008 Trinidad and Tobago Classic was the fourth 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 2008 season. Joe Public entered as the tournament's defending champion.

Every club from the TT Pro League automatically qualified for the competition. In addition, following the conclusion of the National Super League season, the top five 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 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. The 16 teams in the competition, valued at TT$150,000 in total sponsorship, were drawn into four groups, all named after TOYOTA branded vehicles, Terios (Group A), Sirion (Group B), Delta (Group C), and Daihatsu (Group D). All clubs were seeded based on their positions in their respective leagues.

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.

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

The schedule for the 2008 TOYOTA Classic, as announced by the TT Pro League and National Super League:

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.

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