Ser Cauthrien in Dragon Age, when you first fight her while rescuing Anora. When I first stumbed upon the fight, I was shocked at the apparent unfairness of it. Almost 10 Archers, two Mages, several Fighters and Cauthrien herself, who could drop my tank in 2-3 hits. I lost the first few times I tried, but I never waited for the death screen (which wouldn't happen since I was supposed to lose) and always loaded the game when the fight turned sour.
Finally, I ran, kited Cauthrien and her fighters halfway across the level, got them in a small room, disposed of the mooks and started whittling down Cauthrien. Every member of my party died multiple times (thank god for 2 mages with Revive) and I spent a good portion of my diligently hoarded stock of Health Poultices, but by the gods I took her down and then went back to mop up the archers and the mages (combo cast a Storm of the Century and block the only exit out of the room).
Afterwards, I went to the Bioware forums to ***** about the insane difficulty of the fight. I found a thread on that very same subject, where a Bioware dev replied, pointing out that by winning that fight players skipped an entire section of the game (prison escape, which is hilarious), at which point I quietly fired up the game again, loaded the save before the fight and lost it on purpose...