In 1994, twenty-one Caribbean nations gathered to play for the Shell Caribbean Cup. Trinidad and Tobago would emerge victorious, but, in the group stage, Barbados and Grenada would play the tournament's most memorable match— quite possibly the strangest soccer match ever played.
Barbados, Grenada, and Puerto Rico were grouped together in the qualifying round. In their first games, Grenada beat Puerto Rico 2-0 while Barbados lost to Puerto Rico, 1-0. With Grenada and Barbados set to play, the potential outcomes were clear: Grenada would advance with a win. For Barbados to advance, they would need to win by at least two goals because of goal differential being used as a tiebreaker.
There were no draws in the qualifying round, so games went into sudden death “golden goal” extra time. For some inexplicable reason, the tournament organizers decided that extra time goals would be worth two goals. So when Barbados found themselves winning 2-1 in regular time with less than ten minutes left, they had two choices: try and score a third goal, unlikely versus a lock-down Grenada defense, or intentionally score an own goal, knot the game up at 2-2, and hope to score and secure a two-goal victory in extra time. They went with the second strategy, as shown in this video:
With the game tied, 2-2, what was strange became stranger. Grenada realized that a 3-2 win or a 3-2 loss would be equally effective, so they tried to score in either goal — Barbados' or their own. For five frantic minutes, Barbados defended both goals against the two-fronted Grenada assault. Grenada failed, and Barbados netted the game-winner in overtime, winning 4-2 and advancing past the qualifying round.