If TV shows count, seems like Worf pretty much never wins a fight on ST:TNG. Even Guinan was a better shot (think I remember an episode where they are on a phaser range, and Guinan practices at a harder level than Worf does).
Bruce Willis gets punched and kicked silly at the end of Die Hard 2. Of course, Colonel Stewart appears to be something of a Tae Kwon Do expert, while John McClaine is just a bruiser, but he gets soundly trounced and knocked off the wing of the plane. Of course, by then he’d opened the fuel port, which allowed his bruised and bleeding self to blow the plane up in clear violation of the laws of physics, but he lost the fistfight quite badly.
Oh, yeah, jeez, Worf. Well, he did hold his own quite well in unarmed combat against a bunch of Jem’Hadar in that DS9 prison episode, but otherwise he’s pretty pathetic: The Worf Effect - TV Tropes
Didn’t a depowered Superman get his ass kicked by a bully in a diner in Superman 2?
In Barfly, Henry Chinaski (Mickey Rourke) gets beaten in a fight by Eddie the bartender (Frank Stallone), and is left bloody, unconscious and face down in the alley. He later wins a rematch, though.
Mike Newhouse (Adam Goldberg) gets the crap kicked out of him by Clint Bruno (Nicky Katt) in Dazed and Confused.
I’m a believer that Deckard was a replicant (an opinion reinforced by the documentary on the newer released disks) but I figure he was like a Nexus-5 or something. Not quite as advanced.
“Your seat’s in there, four eyes.”
Not quite a fair fight, but there’s also Steve Buscemi in Fargo getting a beatdown from Sheb Proudfoot.
Saving Private Ryan when the Nazi kills the Jew in the abandoned house. Man, that was awful!
A Fair Fight is ambiguous and that’s okay. It could be argued that Rocky vs Apollo Creed was not a fair fight because Sly was an extreme underdog. It was conducted by fair rules, but the participants weren’t equally matched.
But Morbo, what isn’t ambiguous is that Buscema was NOT the hero of Fargo.
Tom Reagan, the character played by Gabriel Byrne in Miller’s Crossing, gets thumped nine ways from Sunday by nearly everyone else with a speaking part in the movie.
Then there’s the titular character from Kick-Ass, who does pretty much anything but throughout most of the film. Though I guess getting a shiv stuck through him is not quite a fair fight.
Um…yeah they were. That’s pretty much the point of the movie…underdog goes the distance with the champ. Both guys took each other to the limit, and Creed won by split decision. If they weren’t evenly matched, somebody would have been knocked out. Perhaps it could be said that Creed was expecting a tomato can, and got caught by surprise, but that’s his fault for being over confident.
I see that you have strong feelings about this subject. 
I like the idea of Fiona. Can’t a girl move beyond her past of fire-bombings and such? Is there no room for redemption? Where else is gal going to get the kind of experience that character needs? I supposed she could have been Mossad, but then she would have to be a real bad girl not to be working for them still. Of course, when they have her be friends with active arms dealers and such, it is harder to overlook her bad qualities. You are making me think to0 hard about this!
Teller in Penn and Teller Get Killed. There’s the great moment when Teller has been practicing ninja kata when Officer McNamara comes in and he ends up on the floor.
According to this IMDB cite, Rocky’s record before fighting Creed was 44-20.
That would strong imply that Creed was a much, much better fighter but that the underdog almost had his day through better prep, lefty punching luck, and the demands of the story line.
In the sequels, Rocky may have been elevated to the top level of heavyweights, but he wasn’t there in the first film.
Any NFL team can beat any other NFL team on a given Sunday. That doesn’t mean the winner is the better team. It just means they won that day.
Fair enough. He went looking for a fight and could’ve been better prepared.
Well, the worst part is that the acting and the writing doesn’t sell me for a minute on her being IRA or anything, for that matter, but an overly-Botoxed and dieted and sunned actress. I might actually be interested if she had real ambiguity and a character as opposed to fashion choices.
Only somewhat related.
There is a movie (perhaps the only one?) where the Duke, aka John Wayne, gets his ass whipped. Actually I think he is killed. Shot down by the bad guys like a dog IIRC. ISTR that he was escorting a bunch of young men from one place to another when the bad stuff went down.
Not terribly related to the OP. But, then again, the times the Duke looses are pretty few…
Although not related to the question of the o.p., I also love the scene where he decides to play Russian roulette with a henchman and proceeds to shoot him in the head.
‘Gay’ Perry: “You…put a live round in that gun?!?”
Harry Lockhart: “Well, yeah, there was like an eight percent chance.”
‘Gay’ Perry: “Eight? Who taught you math?”
My vote is for Brendon in Brick (a neo-noir set in a high school environment), who proceeds to get his ass kicked over and over after picking fights with the local football jock, the enforcer for The Pin in the course of his investigation. The only fights he wins is against a strung out junkie and some random thug who he trips into a post.
Stranger
In The Glass Key, Alan Ladd can’t seem to catch a break any time he find himself in a room with William Bendix.
Well, actually, it turns out he can (jaw, mandible, cheekbone, etc.), but I meant in the other sense.