The 2009 Trinidad and Tobago Pro Bowl was the sixth season of the Digicel Pro Bowl, which is a knockout tournament competition for teams in the TT Pro League. The tournament took place at the conclusion of the 2009 season. Caledonia AIA entered as the tournament's defending champion. The tournament commenced on 17 November 2009 with 10 teams competing in single elimination matches and concluded with the final on 11 December.

Every team based on the island of Trinidad took part in the tournament, with Tobago United as the lone Pro League representative that did not participate. Seeding for this year's competition was determined by each team's league position following the 2009 season. The bottom four teams in the table, United Petrotrin, FC South End, St. Ann's Rangers, and Police entered the tournament in the qualifying round.

The two winning teams from the qualifying round will take on the top two seeds Joe Public and Caledonia AIA, respectively. The other four clubs that qualified for the Pro League Big Six also entered the Pro Bowl directly in the quarterfinals.

The schedule for the 2009 Digicel Pro Bowl, as announced by the TT Pro League:

All matches were played for 90 minutes duration, at the end of which if the match was still tied, penalty-kicks were used to determine the match winner.

On 17 November, St. Ann's Rangers pulled an upset over FC South End 1–0 with Josimar Belgrave providing the lone goal. In the other qualifying round match, Police also stunned United Petrotrin 2–1 to complete the teams in the quarterfinals.

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