List of TT Pro League seasons

However, San Juan Jabloteh ended the possibility of a three-peat when the club finished three points clear of W Connection to win their first league championship in 2002.

The 2006 season saw the closest finish in Pro League history with Joe Public claiming the title by superior goal difference over W Connection after the two teams ended equal on points.

San Juan Jabloteh reclaimed the Pro League title in 2007 after finishing first following the regular season by one point over Caledonia AIA.

The Men from Morvant only earned one point during the Pro League Big Six to give the San Juan Kings a five-point title win.

Joe Public became the second Pro League club to complete the double in 2009, beating W Connection 3–2 in the 2009 FA Trophy final.

The following season, W Connection completed the club's second double with an emphatic 4–1 win over defending champions Defence Force in their next to last match.

Point Fortin Civic became the first club to be expelled from the Pro League after six players appeared for a match late in the inaugural season.

Following the season, FUTGOF were also excluded since the club could not continue to maintain the standards set by the Professional Football League.

Prior to the 2002 season, Doc's Khelwalaas and Police did not follow the remaining six clubs into the newly established TT Pro League.

As a result, two expansion clubs, North East Stars and South Starworld Strikers, were admitted to maintain league membership at eight.

Following the 2007 season, Police withdrew from the league again as a result of commissioner Trevor Paul's directive to ban lawmen from participating in sporting activities.

[12] Police were readmitted into the league following a one-year absence, whereas FC South End were admitted as a new club to replace North East Stars.

[14] North East Stars were readmitted into the Pro League for the 2010–11 campaign following their one-year absence due to the state of their home ground.

Following a runners-up finish in 2009 and being crowned champions in the 2010 seasons, respectively, T&TEC became the third club to gain promotion from the National Super League on 1 March 2011.

In the 2003–04 season, Randolph Jerome (Guyana) of North East Stars became the first foreign player to win the Golden Boot with 28 goals from 36 games.

Jerren Nixon scored an impressive 37 goals in 26 matches in 2004 to help North East Stars to their first Pro League title.

In 2006, the award was again shared between Roen Nelson and Anthony Wolfe of Joe Public and San Juan Jabloteh, respectively, with both scorers finishing with 16 goals in 32 appearances.

[27] During the 2009 season, Kerry Baptiste scored 35 goals in 25 games, including three hat-tricks to give his side Joe Public their second Pro League title.

[30] Jorsling claimed an unprecedented third Golden Boot award following the 2012–13 season after recording 21 goals from 21 matches for Defence Force.

[31] In 2013–14, Marcus Joseph scored 16 goals to secure his first Golden Boot and propel Point Fortin Civic to a fourth-place finish in the club's first year back in the Pro League.