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The decade of the 1950s marked the genesis of the development of football in the Cayman Islands. Long before there were proper football fields and other facilities that modern day players of the game enjoy, the sport’s early followers made do with whatever they could for balls, and wherever there was an open space to play.

By the early 1960s, thanks to the vision of Clifton Hunter and Teacher Timothy McField, two of the Islands’ well-known educators, a football field – the Annex - was built in George Town, Grand Cayman. This helped to promote the development of football in the capital while at the same time Clifton Hunter worked in West Bay, spearheading the growth of the sport in that district.  Thus began an intense rivalry between the two districts which endures to this day.  For a long while, the Annex and the West Bay town hall fields were the main centers for playing football.

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In 1966, the Cayman Islands Football Association was formed, to administer the sport in the Islands, which by then had a growing domestic league.  As the game grew, the need for expanding football facilities became evident. In 1982 the Annex Field, originally built by developer Mike Simmons, was further improved.  The Ed Bush field was built in West Bay and opened by the Queen on March 6, 1994, followed by a memorable game in which the Cayman Islands beat Jamaica to qualify for the finals of the Shell Caribbean Cup in Trinidad & Tobago. Encouraged by this result, Government agreed a build a new football field.

In 1995, the association presided over the further development of the national sports complex, which was transformed into a modern multi-purpose facility, and renamed the Truman Bodden Sports Complex. On July 30 of that year, the Cayman Islands hosted the Shell Caribbean Cup Finals, for the first time, attracting some of the biggest names in world football.  Among the guests were then FIFA President Joao Havelange and the legendary Brazilian hero of the game, Pele. While on this visit, Pele officially opened the Donovan Rankine Field in East End, also built in 1995.  The North Side field came in for redesign and upgrade in 1998/1999 and the G. Haig Bodden Playing Field was completed in Bodden Town shortly afterwards.

Following the destruction caused by Hurricane Ivan in 2004, which left nearly all sporting facilities on the Island destroyed or unusable, the Cayman Islands Government launched a $28million four-year reconstruction project, which has seen all five district stadiums on Grand Cayman, and the Cayman Brac playing field, redeveloped to the highest international standards.  Both the Annex stadium in George Town - now renamed the T.E.McField Sports Centre after its founder - and the Ed Bush Stadium in West Bay are FIFA Two-Star Football Turf facilities, and the Truman Bodden Sports Complex has been reopened as a 3,000 capacity National Stadium.  We now have the facilities to rival any Island in the region, a wonderful achievement for such a small nation.

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As football in the Islands grew, so came the incremental changes for the modernization of the sport. In May 1992, CIFA became a member of CONCACAF, the regional governing body for football and in July of that same year we became a member of FIFA, the international federation for the sport.  Since then, the Cayman Islands Football Association’s international reputation has grown immeasurably as we have competed in  regional and international competitions and our Executive Members have received appointments to major FIFA committees.  Current CIFA President Jeffrey Webb is presently Deputy Chairman of the FIFA Internal Audit Committee, as well as a senior FIFA Match Commissioner.

In 1992, for the first time, the Cayman Islands had a Minister of Sports, the Honorable McKeeva Bush, who a year later appointed a National Sports Committee, headed by current CIFA President Jeffrey Webb.  The Cayman Islands football program had its first paid coach in 1988 with the appointment of Winston Chung of Jamaica as Technical Director. The success of the football program in 1994 also led to further support from Government and in 1995 a full-time, salaried technical director, German national Bernard Schumm, was appointed. This support continues today with the employment of National Technical Director Carl Brown and National Women's Coach Thiago Cunha.

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The CIFA now presides over sixteen domestic league and cup competitions at the under 13 boys, under 15 boys, under 17 boys, under 17 girls, and senior men and women's levels.  There are plans for further expansion in the near future, with grassroots programmes planned for 2011.  In addition to competitions, the CIFA oversees an active calendar of education courses for coaches, referees and administrators, as well as regular camps and training programmes for young players.  Through a wide range of regional and international contacts and partners, we have been able to establish exchange programmes with clubs in Europe and South America, offering players and coaches exposure of football at the highest professional level. 

The CIFA realised two major achievements in 2009, as the under 17 women's national team became the first Cayman Islands team to progress to the finals of a regional competition, participating in the Concacaf Under 17 Women's Championships, and with the opening of the new CIFA office at the Cayman Centre for Excellence; a long-term development that will provide the CIFA with a dedicated training and administration centre.

Presidents

1981-1985 Allan Moore
1985-1987 Ed Bush
1987-1989 Allan Moore
1989-1991 Tony Scott
1991- Present Jeffrey Webb

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