The 2009 TT Pro League season (known as the Digicel Pro League for sponsorship reasons) 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. Police were re-admitted into the league following a one-year absence, whereas FC South End were admitted as a new club. However, North East Stars withdrew siting the state of their home ground, Sangre Grande Recreational Ground, for the past few years as the cause to sit out the season. The Sangre Grande Boys stated that they intend to return to the league for 2010. Furthermore, Caledonia AIA changed the name of the club to Caledonia AIA of Morvant/Laventille. The first goal of the season was scored by Caledonia AIA's Walter Moore against Joe Public in the second minute of the first game on 8 May. Kendall Velox of Caledonia AIA scored the first hat-trick of the season against Police on 23 May. Kerry Baptiste won the Golden Boot by providing 35 goals for Joe Public on their way to becoming league champions. On 12 September, Joe Public used a 2–1 win over W Connection at Manny Ramjohn Stadium to clinch the regular season crown on 41 points. San Juan Jabloteh, Caledonia AIA, W Connection, Ma Pau, and Defence Force all qualified for the Big Six. On 24 October, Joe Public claimed the league title with a 1–1 draw against Caledonia AIA. The achievement marked their second Pro League title with the first coming in the 2006 season. Having finished as the league champion, Joe Public qualified for the 2010 CFU Club Championship. By finishing runners-up in the league, San Juan Jabloteh also qualified for the CFU Club Championship. With an 8–0 loss to W Connection on 1 September, Police finished bottom in the league. The club had a disappointing campaign having only recorded nine points with a -48 goal difference. This marked the first season in which Tobago United did not finish the league season bottom of the table. Furthermore, on 8 January 2010, United Petrotrin announced that they had pulled the club from the Pro League.

Changes from the 2008 season

The following changes were made since the 2008 season:

Teams

Team summaries

Note: Flags indicate national team as has been defined under FIFA eligibility rules. Players may hold more than one non-FIFA nationality.

Player transfers

Managerial changes

Regular season

Competition table

Results

Pro League Big Six

Competition table

Results

League table

Positions by round

Season statistics

Scoring

Top scorers

Hat-tricks

Discipline

Awards

Round awards

Annual awards

The 2009 TT Pro League awards distribution took place on 7 April 2010, at Cascadia Hotel in St. Ann's, Trinidad, prior to the 2010–11 season. Joe Public took home the majority of the league honours including Team of the Year. Eastern Lion Kerry Baptiste was named the league's Player of the Year for the first time in his career, by providing 35 league goals. Baptiste also received the Golden Boot and was named the Best Forward. Joe Public manager Derek King became the youngest manager in the Pro League to win the league championship and claimed the Manager of the Year. In addition, Joe Public's Alejandro Figueroa, Trent Noel, and Keyeno Thomas were named the league's Best Goalkeeper, Best Midfielder, and Best Defender respectively. The remaining team award was won by Caledonia AIA for the Most Disciplined Team of the Year. FIFA international referee, Neal Brizan, won the Referee of the Year for the third consecutive year, whereas Boris Punch won the Match Commissioner of the Year in back-to-back years.