How about this one?
In a 1994 Shell Caribbean Cup match between Barbados and Grenada, Barbados needed to win the match by two goals to advance in the tournament. If they failed, either losing the match or winning by only one goal, their opponent Grenada would advance instead.
A very poorly-conceived though well-intentioned rule governing the tournament stipulated that any goals scored in overtime (and, by virtue of a sudden-death rule, there could only be one) would count doubly. The idea was to reward teams in close matches, so that an overtime victory would be as if a team won by two goals. This simple rule led to a very strange match.
Barbados needed to win by two goals. With less than ten minutes left in the match, Barbados led by exactly two goals and began to play very defensively. In the 83rd minute, Grenada finally scored, making the score 2-1. Barbados tried to answer but, with only three minutes remaining, was unable to score. Members of the Barbados team contemplated their options. To advance, they needed either to score one more goal in the last three minutes (winning by two), or force the game to extra time where a goal would count as if they won by two. Barbados scored on their own net, tying the game at 2-2.
This is not yet the odd part of the match. The Grenada players, initial shock abating, developed their own strategy. If they could score on Barbados in the waning minutes, they would win the match and advance. But, if they could score a goal on themselves, they would lose by one goal which was still enough to advance. For two minutes, Grenada tried to score on either goal, with Barbados players split between defending their own goal and that of their opponents!
Normal time ended in a tie and the game did go to overtime, in which Barbados scored a game winner and advanced (though was eliminated from the tournament in the next round). No penalties for the players' actions in this game were handed down since both teams were earnestly trying to win their group, and the farce was the result of silly incentives.
