Barbados was playing Grenada in the Group round of the Caribbean Cup and was winning 2-0 with seven minutes to go. Grenada then scored, making it 2-1. Even though Barbados was still winning, they were actually losing. Their win would tie the two teams in the standings, but Grenada would win the tiebreaker based on having scored more in previous matches. Barbados had to win by at least two goals or else they were eliminated.
With three minutes to go and Barbados still only winning by one, the team got desperate. Unable to score, they decided to force overtime. Since they were technically winning, the only way to do this was to score on themselves. Which they absolutely did. They didn't even pretend it was an accident; the kicker just kinda dicked around his own net for a bit and then gently lobbed the ball in, his goalie standing there and picking his nose the entire time.
So what? If they score in overtime, it's still just 3-2, and they still don't advance, right? Well, here lies the true reason for this move: The Caribbean Cup scoring policy, which was apparently written after a weeklong rum bender, stated that overtime goals counted double. Not just for this match -- for all matches. That must have been some strong fucking rum, because what ensued due to this rule made a mockery of this (and all) sports.
Caribbean Football Union
Pictured: the thrill of competition, apparently.