In 1994, during the Shell Caribbean Cup qualifiers, Barbados faced Grenada. The tournament organizers had a strange rule: if a match went into extra time, a goal there counted as two - a "golden goal" automatically gave the winner a two-goal difference in the standings. Barbados needed a victory with exactly a two-goal difference to advance to the next round, otherwise Grenada would proceed.
By the 83rd minute, Barbados was leading 2-0 - the difference was already secured. But Grenada scored, making it 2-1, and the necessary margin suddenly disappeared: with this score, Barbados was eliminated. Then, one of the Barbados defenders calmly rolled the ball into their own net - 2-2. A draw with this score sent the game into overtime, where by the rules, the first goal automatically gave Barbados the needed two-goal difference.
Grenada immediately realized the trap: if the score remained 2-2 by the 90th minute, they would be knocked out of the tournament by a single goal scored in extra time. The only way out was to score themselves, in any goal, just to break the tie before the end of regular time. In the last five minutes, Grenada players tried to score anywhere, while Barbados players defended both ends of the field - their own goal and the opponent's. Barbados held on, took the match into overtime, scored the decisive goal there, and advanced with a final score of 4-2.
Each team in this game acted completely rationally - it's just that the rules were set up so that rational behavior looked like sabotage. This exact problem - how to write game rules so that the selfish behavior of participants yields the desired result, not absurdity - is studied by mechanism design theory. In 2007, Leonid Hurwicz, Eric Maskin, and Roger Myerson received the Nobel Prize in Economics for it.
https://kottke.org/23/08/the-weirdest-and-most-chaotic-soccer-match-ever
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