Barbados

Barbados once tried to lose a match on purpose so it could win it.

Nothing else in the team's record matches that afternoon for strangeness, though 1985 comes close for weight: Barbados reached the final of the CFU Championship and lost there to Martinique, the best finish the side has produced. Twenty years later they hosted the Caribbean Cup and went out in the third-place match against Cuba, finishing fourth on home soil.

A World Cup has never followed, but one qualifying campaign came close to changing that story. In July 2000, on the way through the second round for 2002, Barbados beat Costa Rica 2–1, with Llewellyn Riley and Michael Forde scoring the goals; the away leg went 3–0 the other way and the run ended there.

The team plays out of Wildey Turf, known also as the Sir Garfield Sobers Sports Complex, in blue and gold, and has carried the nickname Bajan Tridents through most of its recent history. The Barbados Football Association, which runs the side, dates back to 1910, two decades before the national team's first official fixture, a 3–0 win over Trinidad and Tobago in Bridgetown in 1929.

That opponent has stayed the defining one. Trinidad and Tobago sit closest in the region's football map and in its qualifying draws, and the meetings between the two have carried more history than any other fixture Barbados plays.