Cayman Islands

In June 2024 they beat Antigua and Barbuda 1–0 in qualifying before Cuba ended their run.

The Cayman Islands Football Association, founded in 1966, waited until 1992 for FIFA membership. Home matches are played in front of a few thousand at most at the Truman Bodden Sports Complex in George Town. The team's own history began in 1985, with a goal against Dominica that Lee Ramoon went on to build into a national scoring record of 12. Ian Lindo, who later moved into coaching, and forward Mark Ebanks share the appearance record with 23 caps each.

Their best run in a major tournament came at the 1995 Caribbean Cup, held jointly with Jamaica: a semi-final defeat to Trinidad and Tobago, 2–9, followed by a 0–3 loss to Cuba in the third-place match, leaving them fourth.

In 2000 the federation tried to field eight British-born players, Barry Hayles among them, on the strength of a passport loophole. FIFA ruled the group ineligible for competitive fixtures, and the only game they played together was a friendly defeat to D.C. United.

Bermuda and the British Virgin Islands supply what rivalry the team has, both fellow British Overseas Territories rather than neighbours with a shared border or league. The Cayman Islands have never reached the finals of a World Cup or a Gold Cup.