The TT Pro League is the Trinidad and Tobago professional league for association football clubs. It is the country's primary football competition and serves as the top division in the Trinidad and Tobago football league system. Contested by ten clubs, the league is one of the world's few football leagues that does not operate on an automatic system of promotion and relegation. Seasons run from September to May, with teams playing 18 games each totaling 90 games in the season. Most games are played in the evenings of Fridays and Saturdays, with a few games played during weekday evenings. Pro League clubs also play in other competitions, such as the FA Trophy, League Cup, TOYOTA Classic, Goal Shield, and Pro Bowl against domestic clubs from other divisions; and against clubs from other countries in the CFU Club Championship, the CONCACAF League and the CONCACAF Champions League.
The Trinidad and Tobago League Cup, or commonly known as the First Citizens Cup for sponsorship reasons, is the League Cup style football competition open for Trinidad and Tobago teams competing in the country's TT Pro League. Similar to the FA Trophy, it is played on a knockout basis in September and October towards the beginning of each Pro League season. Unlike the FA Trophy, where 36 teams enter each season from the top three tiers of the Trinidad and Tobago football league system and the Secondary Schools Football League, only teams from the TT Pro League compete in the league cup. The knockout tournament was inaugurated in 2000 and is currently sponsored by First Citizens Bank. Although the league cup is one of the three major domestic trophies attainable by Trinidad and Tobago league teams, it is perceived as a lower priority than the league championship and the FA Trophy. The current theme is Where Winners Reign, with TT$110,000 to the winner, TT$20,000 to the runners-up, semifinal winners receive TT$7,000, quarterfinal winners receive TT$5,000 and Play-off round winners receive TT$3,000.
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 Trinidad and Tobago Goal Shield, or commonly known as the Lucozade Sport Goal Shield for sponsorship reasons, is a knockout tournament competition for football teams competing in the TT Pro League of Trinidad and Tobago. Similar to the First Citizens Cup, it is played on a knockout basis in April and May towards the end of each Pro League season. The structure of the competition not only allows 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 is 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 is 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 knockout tournament is sponsored by Lucozade Sport and is therefore officially known as the Lucozade Sport Goal Shield.
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 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 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 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 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 2011–12 TT Pro League season was the thirteenth season of the TT Pro League, the Trinidad and Tobago professional league for association football clubs, since its establishment in 1999. A total of eight teams contested the league, with Defence Force as the defending champions. The season began on 9 September 2011 and ended on 29 March 2012 with the crowning of W Connection as the league champion. Dexter Skeene, Pro League CEO, announced on 11 February 2011 that by aligning its seasons with those of the major leagues in Europe, the Pro League will afford the opportunity to further link culture with sport to harness and develop the talent of people in Trinidad and Tobago.
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 Classic was the eighth season of the TOYOTA Classic, which is a knockout tournament competition for teams in Trinidad and Tobago's TT Pro League and the National Super League. The tournament began on 23 November with 16 teams competing in single elimination matches until the final on 7 December. W Connection entered as the tournament's defending champion having defeated T&TEC with a penalty shootout after the match ended 0–0.
The 2012–13 Trinidad and Tobago FA Trophy was the 83rd season of the FA Trophy, which is the oldest football competition for teams in Trinidad and Tobago. Caledonia AIA entered as the tournament's defending champion, who defeated Defence Force 1–0 in the 2011–12 final at Manny Ramjohn Stadium. The tournament began on 5 December 2012 with 36 teams competing in single elimination matches and concluded on 1 March 2013 with the crowning of the cup winners.
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 by a score of 4–3 in a penalty shootout after the match ended in 0–0 in regulation during the 2013 final in 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.
Rundell Renold Winchester is a Trinidadian professional footballer who plays for Maltese First Division side Marsaxlokk, where he plays as a forward.
2014 TOYOTA Classic 
