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 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 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 2008 Trinidad and Tobago Pro Bowl was the fifth season of the Courts Pro Bowl, which is a knockout tournament competition for teams in the TT Pro League. W Connection entered as the tournament's defending champion. The tournament commenced on 6 May, with 10 teams competing in single elimination matches and concluded on 23 May, with Caledonia AIA defeating Defence Force 2–0 to claim the title.
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 2013–14 TT Pro League season was the fifteenth season of the TT Pro League, the Trinidad and Tobago professional league for association football clubs, since its establishment in 1999. A total of nine teams contested the league, with Defence Force the defending champions. The season began on 13 September 2013 and concluded on 20 May 2014 with the crowning of W Connection as the league champion.
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 2015–16 TT Pro League season is the seventeenth 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 are contesting the league, with Central FC the defending champions from the 2014–15 season. The season began on 25 September 2015 and concluded on 21 May 2016 with the crowning of Central FC as the league champion.
The 2017 Trinidad and Tobago Pro Bowl was the thirteenth season of the Digicel Pro Bowl, which is a knockout football tournament for Trinidad and Tobago teams competing in the TT Pro League.Defence Force entered as the cup holders having defeated W Connection by a score of 2–1 in the 2016 final. Defence Force won the tournament by 5-3 on penalty kicks over Central after a 2-2 draw at the final whistle.
The 2017 TT Pro League season is the nineteenth 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 are contesting the league, with Central FC the defending champions from the 2016–17 season. The league will start on 9 June and will end on 28 November with the crowning of the champion. North East Stars were crowned champions on the penultimate match day. It was their first league title since 2004.
The 2017 Trinidad and Tobago FA Trophy was the 86th season of the FA Trophy, which is the oldest football competition for teams in Trinidad and Tobago. North East Stars entered as the tournament's defending champion, who defeated W Connection 5-4 on penalties after a 0–0 in the 2014–15 final at Ato Boldon Stadium. The tournament began on 16 September with 64 teams competing in single elimination matches and will conclude with the final on 8 December. W Connection won their 5th FA Trophy after beating Police 3-1 in the final at the Ato Boldon Stadium.
The 2017 Trinidad and Tobago League Cup was the eighteenth season of the First Citizens Cup, which is the league cup competition for Trinidad and Tobago teams competing in the TT Pro League. Defence Force entered as the cup holders having defeated Ma Pau Stars by a score of 1–0 in the 2016 final. First Citizens Bank changed the slogan to "Where Winners Reign" due to the amount of money that the winner of the tournament would obtain. Teams were drawn into numbers with respect to their position in the 2017 TT Pro League at the time of the draw. It means that teams from 7–10 in the league enter at the play-offs, while from 1–6 enter at the quarterfinal stage. W Connection were crowned 8-time champions after defeating Defence Force in the final.
The 2018 TT Pro League season is the 20th 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 are contesting the league, with North East Stars the defending champions from the 2017 season.
