2009 Trinidad and Tobago Cup
| Country | Trinidad and Tobago | ||
|---|---|---|---|
| Teams | 32 | ||
| Defending champions | Caledonia AIA | ||
| Champions | Joe Public (PL) | ||
| Runners-up | W Connection | ||
| Matches played | 31 | ||
| Goals scored | 133 (4.29 per match) | ||
| Top goal scorer(s) | Conrad Smith (8 goals) | ||
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The 2009 Trinidad and Tobago Cup was the 80th 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 2009 TT Pro League season. Caledonia AIA entered as the tournament's defending champion. The tournament commenced on 15 November, with 32 teams competing in single elimination matches and concluded on 9 December.
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 2009 season all qualified for the competition. In addition, the top seven finishers from the Super League also qualified. However, only three clubs from 5 of the 6 regional football associations were awarded qualification into this year's edition, with the Tobago FA as the exception as they only received two.
The following clubs qualified for the 80th 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 2009 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 2 November 2009 at its head office in Port of Spain, Trinidad with ties played in the week beginning 15 November 2009. The only Pro League match-up featured W Connection against FC South End. As a result, seven Pro League clubs advanced to the next round with little difficulty. The lone upset of the round occurred when Joe Public from the Eastern FA Premier Division defeated Club Sando of the National Super League.
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