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This is a list of Trinidadian football transfers during the 2009 season. Only moves featuring at least one TT Pro League club are listed. Transfers that were made following the conclusion of the 2008 season on 29 November 2008 and during the 2009 season, which ran until 27 October 2009, are listed.
Players without a club cannot join one at any time, either during or in between transfer windows. Clubs within or outside the Pro League may sign players on loan at any time. If need be, clubs may sign a goalkeeper on an emergency loan, if all others are unavailable.
All players and clubs without with a flag are from Trinidad and Tobago. In addition, transfers involving Major League Soccer clubs in the United States and Canada technically have the league as the second party and not the listed club. MLS player contracts are owned by the league and not by individual clubs.
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 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 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 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 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 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 2012–13 TT Pro League season was the fourteenth 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 W Connection the defending champions. The season began on 14 September 2012 and ended on 10 May 2013 with the crowning of Defence Force as the league champion.
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 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 history of the TT Pro League has its roots spanning back to the 1970s and 1980s when Trinidad and Tobago experienced an upswing in support for its domestic football. Several of the national team players featured for Defence Force during its dominance of the National League, which included the Teteron Boys becoming the first Trinidadian and only second club from CONCACAF to accomplish the continental treble in 1985. In addition, the national team also rose to prominence in the late 1980s after falling short by one match of qualification for the nation's first FIFA World Cup in 1989. Optimism for the growth and community interest of football in Trinidad and Tobago was at an all-time high. However, the early 1990s would mark a low point in Trinidad and Tobago football. In 1993, after a streak of poor performances, the Soca Warriors gave its worst ever showing in the 1993 Caribbean Cup after finishing a disappointing third, which was preceded by an early exit from its '94 for Sure campaign to qualify for the 1994 FIFA World Cup hosted in the United States.