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My worst timing conundrum was a tourney with the following rules:
1) No run rule
2) 1:15 time limit - no inning shall start after 1:15 has elapsed.
3) 1:35 time limit - if you reach this, then the game reverts to the last completed inning.
4) No ties - this was a tourney - we used international rule for extra innings (runner on 2nd) in addition to all batters beginning with 3-2 count.
5) Pitchers could not pitch in consecutive games, except for extra innings, and except for the semifinals and finals - played the following day.
The problem occurred when in the 2nd round, both teams had awful pitchers available (both used their 2 top pitchers to survive round 1) . The top half of the 1st took about 45 minutes, as the visitor scored 43 runs. Then, the bottom half was still going as 1:35 expired. I don't remember the exact score, but home had not surpassed 43 at that point. Obviously we were unable to fulfill ALL of the ground rules. Visiting team wanted to play on (they had 2 outs). Home team wanted the game ruled over, revert back to no score, replay the GAME (allowing him to get at least one of his good pitchers in), or calling the game "over", but tied - again allowing the good pitchers back in for an extra inning.
It was a mess - we called the UIC and the tourney sponsor over to see which "rule" they wanted us to break - we ended up just finishing the inning (I think that was the most fair way of fixing the mess). Home team won by scoring 44.
These two teams met again in the championship, and home won again in a much lower scoring game with their good pitchers in place.
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