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Twenty20 domestic cricket first appeared in an organised manner in the West Indies in 2006 with the privately organised Stanford 20/20. The second and last edition of the Stanford competition was officially made part of the West Indies Cricket Board (WICB) calendar in 2008, after which the tournament ended when its sponsor Allen Stanford was charged with fraud and arrested in June 2009. The next organised Twenty20 competition came about with the creation of the Caribbean Twenty20 tournament by the WICB. The Caribbean Twenty20 was created to fill the gap left by the end of the Stanford 20/20 and to coincide with the 2010 Champions League Twenty20 tournament, which started less than two months after. The top domestic team from the Caribbean Twenty20 tournament qualified for the Champions League as the sole representative of the West Indies.

The WICB first announced the plans for the Caribbean Premier League in September 2012 when it was revealed that the board was "in the advanced stages of discussions to have a commercial Twenty20 league in the region" with an unnamed investor and hoped to conclude a deal before 30 September. On 14 September, the board met to make decisions on the structure and organisation of the Caribbean Twenty20 CPL Schedule in January; to discuss the governance structure of the board and also discuss the planned commercial Twenty20 league and to finalise its structure. The Federation of International Cricketers' Associations (FICA) and the West Indies Players Association (WIPA) were also to be brought in to discuss issues pertaining to players in relation to the planned T20 league. On 13 December 2012, the WICB announced that they had finalised an agreement with Ajmal Khan founder of Verus International, a Barbados-based merchant bank, for the funding of the new franchise-based Twenty20 league to be launched in 2013. It was then expected that the new Caribbean Premier League was likely to comprise six Caribbean city-based franchises as opposed to the current territorial set-up with the majority of the players are to come from the West Indies. As part of the agreement, the WICB will receive additional funding from Verus International for additional retainer contracts for players in addition to the 20 annual retainer contracts the board currently funds.

Dates for the tournament were confirmed for the 2013 Caribbean Premier League as 29 July to 26 August. The 2014 and 2015 tournaments took place between 5 July to 10 August and 21 June to 26 July respectively and the 2016 tournament took place between 29 June to 7 August.