In 2006 and 2008, the Cayman Islands played in the Stanford 20/20 tournament (where matches had full Twenty20 status).[10] In the World Cricket League (WCL), Cayman Islands debuted in Division Three in 2007 but subsequently fell as low as Division Six before the WCL was abolished. The Caymans currently play in ICC Americas regional qualification tournaments.
In April 2018, the ICC decided to grant full Twenty20 International (T20I) status to all its members. Therefore, all Twenty20 matches played between the Cayman Islands and any other ICC member after 1 January 2019 are eligible for T20I status.[11]
The Cayman Islands gained associate membership of the ICC in 2002, a year in which they finished third in the Americas Championship in Buenos Aires, Argentina after recording wins against Argentina, the Bahamas and Bermuda.[14] The 2004 Americas Championship served as a qualifying competition for the 2005 ICC Trophy, and a repeat of their third-place finish from 2002 would have qualified them for that tournament. Wins against Argentina and the Bahamas meant they could only finish fourth however.[15] This did qualify them for a place in a repêchage tournament in early 2005 in Kuala Lumpur, Malaysia. They finished fifth in that tournament after beating Kuwait in a play-off match.[16]
Later in 2005, the Cayman Islands took part in the ICC Intercontinental Cup, a tournament for ICC associate members with first-class status. They lost both their first round matches to Bermuda and Canada, thus not qualifying for the semi-finals.[17] In 2006, they first played in the inaugural Stanford 20/20 tournament. They beat the Bahamas in the preliminary round,[18] but lost to Trinidad & Tobago in the first round proper.[19]
In August 2006, they finished third in Division One of the ICC Americas Championship after wins against Argentina and Canada.[20] This qualified them for 2007 Division Three of the World Cricket League, which was played in May/June 2007 in Darwin, Australia. After beating Hong Kong and Tanzania in the first round, they lost to Argentina in the semi-finals, and to Papua New Guinea in the third place play-off, thus finishing fourth in the tournament.[21] In 2009 they again placed in 2009 Division Three in which they came 5th thus relegating to Division Four. Like Argentina their bad run continued and again finished fifth only winning over Argentina. In 2012, they managed to stop the fall, finishing fourth in 2012 Division Five.
2018-Present
In April 2018, the ICC decided to grant full Twenty20 International (T20I) status to all its members. Therefore, all Twenty20 matches played between Cayman Islands and other ICC members from 1 January 2019 have been full T20I matches.[22]
The Cayman Islands played their first T20I match against Canada on 18 August 2019, after finishing second in the Southern sub region qualification group and advancing to the Regional Final of the 2018–19 ICC World Twenty20 Americas Qualifier tournament.[23]