[3] Modern football in the Cayman Islands is generally attributed to the efforts of local school teacher, and later principal, Timothy McField in the late 50s and early 1960s.
With the help of a road builder named Mike Simmons, the two constructed the islands first competitive pitch, known originally as the Annex, from swamp land near the school in George Town.
[7] The territory joined FIFA in 1992[8] and played their first World Cup qualifying match at home against Cuba on 11 November 1996, losing 0–1.
[9] Jeffrey Webb, Former president of CONCACAF, Cayman Islands Football Association (CIFA), and FIFA vice president, was arrested for corruption charges on 27 May 2015 by Swiss police acting at the request of the U.S. Department of Justice on charges of racketeering, wire fraud and money laundering conspiracy.
[12][13] Professional football in the Cayman Islands is organized by the national federation and currently consists of two leagues.