The first cricket match between colonies was played in 1865, but the game had been played in the Caribbean for almost half a century by then. By 1900, a triangular series was being held between Demerara, Barbados, and Trinidad, but transport between the islands remained the major obstacle to expansion and it wasn't until after the Second World War when air transport became readily available that Jamaica began to play regular games against other islands.

In 1956, British Guiana hosted a four-team knock-out tournament, and this was repeated five years later with the Combined Islands added. But the problems of traveling between the islands made a regular domestic competition unworkable until the advent of cheap and reliable air travel.

Until the Shell Shield (named after Royal Dutch Shell) was launched in 1965-66, there had been games between islands but they were not part of any competition. The five sides which had contested the 1961 knock-out competed in a round-robin league, with two home matches and two away matches. The format and sponsor remained unaltered until 1981-82 when Combined Islands were split after their maiden success the previous year. Until then, Barbados had dominated with nine titles out of 14. Barbados' dominance continued through the 1980s, and in 1986-87 the competition was restructured into two groups with a final. That was short-lived, and the league was back under a new sponsor in 1987-88, and from 1989-90, when Leeward Islands won their first title, no side established a stranglehold.

Tinkering with the format rumbled on, with a final in 1995-96, a ten-match round-robin the following year and then a five-match event after that as no sponsor could be found. In 1998-99 Busta, a soft drink manufacturer, came on board and the format again changed, with a semi-final and final appended to the league matches. The 2000s also had teams from other countries included - as England A, Bangladesh A, India A and Kenya all played - as well as a West Indies B team built around university students. The B side was ditched in 2004-05 and a round-robin format and a one-off final returned.

Year Winner
1965-66 Barbados
1966-67 Barbados
1967-68 No competition
1968-69 Jamaica
1969-70 Trinidad
1970-71 Trinidad
1971-72 Barbados
1972-73 Guyana
1973-74 Barbados
1974-75 Guyana
1975-76 Trinidad / Barbados
1976-77 Barbados
1977-78 Barbados
1978-79 Barbados
1979-80 Barbados
1980-81 Combined Islands
1981-82 Barbados
1982-83 Guyana
1983-84 Barbados
1984-85 Trinidad & Tobago
1985-86 Barbados
1986-87 Guyana

Year Winner
1987-88 Jamaica
1988-89 Jamaica
1989-90 Leeward Islands
1990-91 Barbados
1991-92 Jamaica
1992-93 Guyana
1993-94 Leeward Islands
1994-95 Barbados
1995-96 Leeward Islands
1996-97 Barbados

Year Winner
1997-98 Leeward Islands / Guyana

Year Winner
1998-99 Barbados
1999-00 Jamaica
2000-01 Barbados
2001-02 Jamaica

Year Winner
2002-03 Barbados
2003-04 Barbados
2004-05 Jamaica
2005-06 Trinidad & Tobago
2006-07 Barbados
2007-08 Jamaica

Year Winner
2008-09 Jamaica
2009-10 Jamaica
2010-11 Jamaica
2011-12 Jamaica
2012-13 Barbados
2013-14 Barbados
2014-15 Guyana
2015-16 Guyana