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So many.
Curse of Strahd in 3.5: Who knew Con damage to a mostly spell caster group could be dangerous not just once but 4 times. In comparison both fights were Strahd were a f**ing walk in the park.
More of a test game than an actual campaign: We were testing if a CR appropriate group of goblins with levels vs a group of players would play out for the players: Well as it turns out I suck at calculating CR so our first fight was 5 players vs 5 goblins level 15 (Same as players) plus 10 starting goblins. We adjusted it for a correct CR and it was still a massacre. Ambush is a HELL of an advantage.
Anything goes campaign. Well turns out anything goes for the DM too so Level 3 half colossal half minotaur barbarian opponent with a posse of gobs with a ballista safely away means players die every other round or so.