The Trinidad and Tobago Pro Bowl, or commonly known as the Digicel Pro Bowl for sponsorship reasons, is a knockout football tournament for teams in the TT Pro League. The competition is played during May following the conclusion of the Pro League season. The Pro Bowl began without a sponsor during the competitions's first two years. It was not until 2006, when Courts began providing monetary prizes, that the tournament had its first sponsor. Following a pullout by Courts after three years, Digicel became the new branding partner of the competition. The prize money for the winner, as announced by TT Pro League CEO Dexter Skeene, is determined by the players, the clubs and the communities. With this programme the communities are expected to adopt the clubs and pledge their support to them during the tournament. The prize money will be the amount received from gate receipts and TT$100,000, courtesy of tournament sponsors Digicel.
The 2009 TT Pro League season was the eleventh season of the TT Pro League, the Trinidad and Tobago professional league for association football clubs, since its establishment in 1999. A total of eleven teams contested the league, with San Juan Jabloteh the defending champions. The season began on 8 May, with Super Friday, and ended on 27 October. The format of the season was changed from each club playing three rounds to two rounds in the regular season to facilitate the national team with its attempt to qualify for the 2010 FIFA World Cup.
The 2009 Trinidad and Tobago Goal Shield was the inaugural season of the Lucozade Sport Goal Shield, which is a knockout tournament competition for teams in the TT Pro League. The structure of the competition not only allowed the winners and runners-up healthy purses at the end of the tournament, but more so give an added incentive for more goals to be scored throughout the tournament. In particular, the winner of the competition was awarded TT$20,000 plus an additional TT$3,000 for every goal scored in the final, TT$2,000 for every goal in the semifinals, and TT$1,000 for each goal scored in the quarterfinals. Whereas, the runner-up was awarded TT$10,000 plus TT$1,500 for every goal scored in the final, TT$1,000 for every goal in the semifinals, and TT$500 for each goal scored in the quarterfinals.
The 2010–11 TT Pro League season was the twelfth season of the TT Pro League, the Trinidad and Tobago professional league for association football clubs, since its establishment in 1999. A total of eleven teams contested the league, with Joe Public the defending champions. The season began on 23 April 2010 and ended on 1 February 2011 with the crowning of the league champion. The league calendar was changed for the second consecutive season. Pro League CEO, Dexter Skeene, announced on 25 March 2010 that the Pro League Big Six competition was to be discontinued to increase attendances and importance of league matches, which would be moved exclusively to Fridays and Saturdays.
The 2008 TT Pro League was the tenth season of the TT Pro League, the Trinidad and Tobago professional league for association football clubs, since its establishment in 1999. A total of ten teams took part in the league, with San Juan Jabloteh the defending champions. The season began on 5 April and ended on 29 November, with the conclusion of the Lucozade Sport Big Six.
The 2008 Trinidad and Tobago League Cup was the ninth season of the First Citizens Cup, which is the league cup competition for Trinidad and Tobago teams competing in the TT Pro League. The slogan for the year's league cup was No Room for Losers and was sponsored by First Citizens Bank for the eighth consecutive year. W Connection entered as the defending champions after having defeated Caledonia AIA 2–0 in the 2007 final for their fourth consecutive league cup title.
The 2009 Trinidad and Tobago League Cup was the tenth season of the First Citizens Cup, which is the league cup competition for Trinidad and Tobago teams competing in the TT Pro League. Continuing from previous seasons, the slogan for the year's league cup was No Room for Losers and was sponsored by First Citizens Bank for the ninth consecutive year. To keep with the tag-line, this year's edition will only reward prizes to the cup winners and runner-up. The Savonetta Boys of W Connection entered as the five-time defending cup holders by winning the 2008 league cup over Joe Public 6–5 in a penalty shootout after the match ended 2–2 in regulation.
The 2007 TT Pro League was the ninth season of the TT Pro League, the Trinidad and Tobago professional league for association football clubs, since its establishment in 1999. A total of ten teams took part in the league, with Joe Public the defending champions. The season began on 14 April and ended on 18 December, with the conclusion of the Lucozade Sport Big Six.
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.
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.
The 2009 Trinidad and Tobago FA Trophy 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 2010–11 Trinidad and Tobago FA Trophy was the 81st season of the FA Trophy, which is the oldest football competition for teams in Trinidad and Tobago. Joe Public entered as the tournament's defending champion, who defeated W Connection in the 2009 final. The tournament commenced on 17 November 2010, with 32 teams competing in single elimination matches and concluded on 25 January 2011.
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 football 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.
The 2008 Trinidad and Tobago FA Trophy 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 2010 Trinidad and Tobago Goal Shield was the second edition of the annual Lucozade Sport Goal Shield, which is a knockout tournament competition for teams in the TT Pro League. W Connection entered as the defending champions after they defeated Defence Force 3–0 in the inaugural tournament. Continuing from the previous season, the competition not only allowed the winner and runner-up healthy purses at the end of the tournament, but more so give an added incentive for more goals to be scored throughout the tournament. In particular, the winner of the competition was awarded TT$20,000 plus an additional TT$3,000 for every goal scored in the final, TT$2,000 for every goal in the semifinals, and TT$1,000 for each goal scored in the quarterfinals. Whereas, the runner-up was awarded TT$10,000 plus TT$1,500 for every goal scored in the final, TT$1,000 for every goal in the semifinals, and TT$500 for each goal scored in the quarterfinals.
The 2011–12 Trinidad and Tobago FA Trophy was the 82nd season of the FA Trophy, which is the oldest football competition for teams in Trinidad and Tobago. San Juan Jabloteh entered as the tournament's defending champion, who defeated North East Stars 1–0 in the 2010–11 final at Marvin Lee Stadium. The number of entrants in the tournament was expanded by the Trinidad and Tobago Football Association to allow four teams from the Secondary Schools Football League to compete in the competition against semi-professional and professional football clubs. The tournament began on 29 January 2012 with 36 teams competing in single elimination matches and concluded on 25 March 2012.
The 2011 First Citizens Cup was the twelfth season of the First Citizens Cup, which is the league cup competition for Trinidad and Tobago teams competing in the TT Pro League. Continuing from previous seasons, the slogan for the year's league cup was No Room for Losers and was sponsored by First Citizens Bank for the eleventh consecutive year. To keep with the tag-line, the year's edition only rewarded prizes to the cup winners and runner-up. Joe Public, as the defending cup holders, did not enter the competition after the club withdrew from the Pro League citing financial difficulties. The Eastern Lions defeated Defence Force in the 2010 final.
The 2012 Trinidad and Tobago Goal Shield was the third season of the Lucozade Sport Goal Shield, which is a knockout tournament competition for Trinidad and Tobago teams competing in the TT Pro League. North East Stars entered as the Goal Shield holders after defeating San Juan Jabloteh 1–0 in the 2010 final. Continuing from previous seasons, the competition not only allowed the winner and runner-up healthy purses at the end of the tournament, but more so give an added incentive for more goals to be scored throughout the tournament. In particular, the winner of the competition was awarded TT$20,000 plus an additional TT$3,000 for every goal scored in the final, TT$2,000 for every goal in the semifinals, and TT$1,000 for each goal scored in the quarterfinals. Whereas, the runner-up was awarded TT$10,000 plus TT$1,500 for every goal scored in the final, TT$1,000 for every goal in the semifinals, and TT$500 for each goal scored in the quarterfinals.
The 2014 Trinidad and Tobago Goal Shield was the fifth season of the Lucozade Sport Goal Shield, which is a knockout tournament competition for Trinidad and Tobago teams competing in the TT Pro League. W Connection entered as the cup holders having defeated North East Stars 4–3 in a penalty shootout in the 2013 final. Continuing from previous seasons, the competition not only allowed the winner and runner-up healthy purses at the end of the tournament, but more so give an added incentive for more goals to be scored throughout the tournament. In particular, the winner of the competition was awarded TT$30,000 plus an additional TT$3,000 for every goal scored in the final, TT$2,000 for every goal in the semifinals, and TT$1,000 for each goal scored in the quarterfinals. Whereas, the runner-up was awarded TT$10,000 plus TT$1,500 for every goal scored in the final, TT$1,000 for every goal in the semifinals, and TT$500 for each goal scored in the quarterfinals.
The 2014 Trinidad and Tobago Pro Bowl is the tenth season of the Digicel Pro Bowl, which is a knockout football tournament for Trinidad and Tobago teams competing in the TT Pro League. For the fourth consecutive season, the Pro Bowl concluded the Pro League calendar. Additionally, for the third year the winner of the Pro Bowl was invited to compete in the Digicel Charity Shield to open the 2014–15 Pro League season. W Connection entered as the Pro Bowl holders, having defeated North East Stars 4–3 in a penalty shootout after the match ended in 0–0 in regulation during the 2013 final at Hasely Crawford Stadium. The competition commenced on 2 May with all nine Pro League teams competing in single elimination beginning with the qualifying round and concluded on 23 May with the final.
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