The 2008 Trinidad and Tobago Cup was the 79th season of the FA Trophy, which is the oldest football competition for teams in Trinidad and Tobago. The tournament took place at the conclusion of the 2008 season. Joe Public entered as the tournament's defending champion. The tournament began on 3 December, with 32 teams competing in single elimination matches.

The tournament featured teams from the top three levels of the football pyramid. These three levels and 8 leagues, namely the TT Pro League, National Super League, Central FA's Premier Division, Eastern FA's Premier Division, Eastern Counties' Football Union, Northern FA's Premier Division, Southern FA's Premier Division, and Tobago FA's Premier Division, each have their own separate qualification process to trim their ranks down to their final team delegations.

The top eight finishers in the Pro League for the 2008 season all qualified for the competition. In addition, the top eight finishers from the Super League also qualified. However, only three clubs from 4 of the 6 regional football associations were awarded qualification into this year's edition, with the Eastern Counties and Northern FA as the exceptions as they only received two.

The following clubs qualified for the 79th edition of the FA Trophy:

Eastern FA – Premier Division

Eastern Counties – Football Union

Southern FA – Premier Division

Tobago FA – Premier Division

The schedule for the 2008 FA Trophy, as announced by the Trinidad and Tobago Football Association:

All matches were played over two 45 minute halves, and in the process if the match were drawn at the end of regulation time, then two additional 15-minute halves were used, and if necessary, penalty kicks if still drawn after extra time.

The draw for the most prestigious knockout tournament held by the Trinidad and Tobago Football Association was made on 24 November 2008 at its head office in Port of Spain, Trinidad with ties played on 3 December 2008. The only Pro League match-up featured United Petrotrin against North East Stars. All Pro League clubs advanced easily into the second round with a combined scoreline of 28–2. With the withdrawal of Trinidad and Tobago U20, Charlotteville Unifiers was the lone survivor facing competition from a higher division.

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