Round 1: Match 8
Jason and the Argonauts vs. some skeletons
Movie: Jason and the Argonauts
http://www.youtube.com/watch?v=RwBc2K2dw-8
Classic Ray Harryhausen work, possibly the best piece of stop motion animation ever. Before the time where this would be done with computers, Jason and the Argonauts fight stop motion skeletons that move, fight, grab weapons, die, jump over things, almost seem sentient. While it might not look as fancy as it would if it were done today, it still holds up as being damn impressive.
VS
William Munny vs. Little Bill and co.
Movie: Unforgiven
http://www.youtube.com/watch?v=h_NrMBdNp88
The whole movie seems to build to this, while managing to catch Munny at least by surprise. It's excellently shot and has a lot more suspense than gun fights that are just people shooting from behind things and ducking bullets like a lot of other westerns might have done (*cough*ALL JOHN WAYNE MOVIES*cough*). Capped by one of my favorite Eastwood lines.