I played a three-way match of Warfleets once with about ~25 ships on the field plus all their accompanying squadrons–which is a respectable game with each fleet being a little on the larger size. With only 4 rounds in a game normally, you’d expect things to be pretty cut-and-dry as to who will win after the first couple rounds but in this meat-grinder of a game it all came down to one singular morale roll at the end of round 4. Every other ship had been wiped from the board and the only deciding factor on whether it was a three-way draw or a win for one of the players was a 4+ on a 6-sided die on the last remaining ship carrying a scoring objective.
He made it!
My most memorable would have to be the first Frostgrave 2e game I played with a buddy. We were using a custom board I built and plenty of beautiful terrain, both with fully painted warbands. We were both in it for some casual fun, as our normal wargame group had been nothing but semi-competitive Marvel Crisis Protocol for about two years. We played it for fun, narratively and casually, and both agree it was the best wargaming experience we’d had in a long time. In the end, it was pretty much a tie. I technically won, but when calculating XP gains and gold for the mission, the only difference was me coming out with 5xp more than him.