Trinidad & Tobago Premier League

Prior to the 1990s, professionalism in Trinidad and Tobago football was non-existent. In the 1970s and 1980s, the National League, composed primarily of amateur players, served as the highest level in the Trinidad and Tobago football league system. However, it was during this period Trinidad and Tobago experienced an upswing in support for football following a rise in international success at both club and national team levels. In 1985, Defence Force became only the second team from CONCACAF to accomplish the continental treble after the club won the National League, FA Trophy, and CONCACAF Champions' Cup. Coupled with the Strike Squad's near qualification for the 1990 FIFA World Cup, optimism for the country's first appearance at the World Cup was at an all-time high.

However, the early 1990s marked 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 Caribbean Cup after finishing a disappointing third, which was preceded with an early exit from its 1994 FIFA World Cup qualification attempt. In response, Trinidadian and former FIFA vice-president Jack Warner spoke out describing Trinidad and Tobago's football as being "in shambles" and crowd support was "non-existent".

In November 1995, Jack Warner proposed that creating a professional league to produce homegrown players would function as the building blocks to qualify for the 1998 FIFA World Cup in France. In fact, speaking on the importance of a professional league for the future, Warner stated "professionalism or death for Trinidad and Tobago football." His proposal, which included the clubs' ability to operate as business entities, laid the foundation for professional football in Trinidad and Tobago.

In order to successfully develop a professional football league in the country, the Trinidad and Tobago Football Association established the Semi-Professional League in 1996 to provide teams and players with a semi-professional environment, as they transitioned during a three-year period for life in a professional league. In particular, clubs were issued three important criteria that would be used for professional league admission:

• The incoming club must show proof of a home venue to stage matches,
• The incoming club must provide a minimum wage of TT$2,000 per month to a contracted player,
• The incoming club must have a minimum of sixteen (16) contracted players, a manager, and a physiotherapist.

After the final season of the Semi-Professional League, several clubs were denied admission after failing to meet the aforementioned criteria. Clubs were also faced with supplying the professional league a bank draft guaranteeing TT$400,000 for admission.

The Trinidad and Tobago all-professional league, called the Professional Football League, was founded on 5 January 1999 with its inaugural season held in the same year to become the first professional football league in the Caribbean. The eight inaugural members were Defence Force, Doc's Khelwalaas, FUTGOF, Joe Public, Point Fortin Civic, Police, San Juan Jabloteh, and W Connection. In the first professional season, Defence Force continued a theme set during the 1970s, 1980s, and early 1990s, which saw the club win a record twentieth league championship.

The Professional Football League would continue for two more seasons before a decision from its owner and founder, Jack Warner, to withdraw funding for the league. Early league results suggested an improvement in player development with several domestic professionals named to starting roles in the national team. Consequently, club owners agreed in March 2012 to develop a new professional league that would operate rather as a corporation, known as the T&T Pro League Limited, owned by the member clubs and a continuation of the Professional Football League. One month later, the TT Pro League began with eight members: Arima Fire, Caledonia AIA, Defence Force, Joe Public, North East Stars, San Juan Jabloteh, South Starworld Strikers, and defending champions W Connection.

After establishing itself on the talents of homegrown players during its initial years, the league continued to see several of its stars move to leagues in Europe and North America. Collin Samuel was the first to leave when he signed for Falkirk in August 2002, and was joined at Dundee United a year later by Jason Scotland. Kenwyne Jones, former standout for Joe Public and W Connection, signed with Southampton, whereas Cornell Glen of San Juan Jabloteh joined the MetroStars of Major League Soccer during the 2004 season. The departures ultimately benefited the Pro League as the national team, composed of several current and former Pro League players, qualified for the nation's first FIFA World Cup in November 2005.

In the build-up to the 2006 FIFA World Cup, community interest in local football was at an all-time high and the Pro League garnered praise for its development of homegrown professional footballers. As a result, the league implemented a series of marketing plans to establish itself as a viable professional league. Two major initiatives were to increase league membership back to ten teams and establish a reserve league in 2007 for players that were previously on the bench during league matches to have a league of their own to show scouts their skills on the field.

After the league's first decade, the TT Pro League has taken steps to internationalise the league in an effort to raise the level of its competition. One of the first moves in this regard was to align its calendar with those of major football leagues around the world. Prior to 2011, the Pro League operated on a spring-to-fall format which caused several conflicts with the FIFA calendar. Consequently, many of the league's top players abandoned their Pro League clubs during June and July to compete in international competitions, which made it difficult for the league to attract supporters for its matches. The schedule change has provided several players greater transfer opportunities to more prominent leagues. The second move was to expand club rosters from 25 to 35 players to provide clubs flexibility during the prolonged calendar featuring three rounds of league competition, five domestic cup competitions, CFU Club Championship, and the CONCACAF Champions League.

The Pro League has also started to market itself on the talents of its Trinidad and Tobago players, both experienced and young talents. Beginning in 2009, the league witnessed a return of several former national team stars, including Stern John, Russell Latapy, Dennis Lawrence, and Dwight Yorke. Several more Pro League players have made a significant impact on the league after spending a majority of their career on the twin-island Republic. In the 2009 season, Arnold Dwarika of United Petrotrin became the first Trinidadian player to score 100 Pro League goals. Moreover, breakout stars such as Keon Daniel, Cornell Glen, Kevin Molino, and Lester Peltier began making names for themselves in the Pro League before starring for the Soca Warriors and securing transfers to Asia, Europe, and North America. This exchange of top prospects for veterans to the Pro League signifies an increased international awareness and potential for popularity.