The classic I recall being reported for the old S&T game “Grunt” (a brilliant game, later modernised as “Search and Destroy”) was the player who, insisting that there was no rule saying that the six-strong squads had to be removed from play after six KIA or WIA had been inflicted on them, proceeded to surround an enemy squad and inflict 36 casualties on it, all worth victory points. I imagine that this sort of thing is what inspired later SPI rules writers to stipulate things like the expenditure of movement points entitling a unit to move from one hex to an *adjacent* hex, rather than just “another hex”.
“Grunt” also had a scenario that the US player could win by declaring, by turn 4, that this was the “day-to-day” scenario, and no enemy were present. Unfortunately the number of counters in the NLF order of battle was different for each scenario, so it was possible to tell this rather easily just by counting the number of enemy units on the map. Easy enough to fix by making all the NLF orbats up to the same number with dummies, of course. Several other games have “broken” scenarios — SPI’s “Raid!” and VG’s “Panzer Command” both include scenarios that, if one bothers with a little simple time-and-distance analysis, one side cannot possibly win if their opponent knows what they are doing.
A rule interpretation that annoyed me was one a friend of mine made in a game of SPI’s excellent “Fighting Sail”. He used a “wear ship” maneouvre counter to put himself in an advantageous position, and I pointed out that he hadn’t put the stern of his ship through the wind. He (being a better rules lawyer than sailor) maintained that he didn’t have to. We checked the rules, and he appeared to be right! One hopes it was picked up in errata eventually.
Not an interpretation, but the rules themselves — I wish I could remember which set of naval rules stated that ships could never increase or decrease speed by more than half their current speed. It sounds as if it might be a sensible rule, until you realise that it means that ships in motion can never stop, and stopped ships can never move.
And then there are the weird torpedo rules in “Submarine” that meant that there were numerous pairs of points on the sea surface that could not be connected by a straight line…
All the best,