Rush Limbaugh and friends vs. Borris Yeltsin and a bottle of vodka?
Boris would down the bottle, and start calling Rush and pals “Moose and Squirrel”. In the ensuing laughter, Boris’d smash the empty bottle and gut them all with it. Boris wins!
Voyager’s EMH vs Red Dwarf’s Rimmer
Rimmer exhausts the EMH’s battery power with tales of “Risk” dice rolls.
next up, BBSs vs. EZBoards?
EZBoards wins due to a no-show. I haven’t seen a BBS in years (ah, the days of Procomm Plus!).
The Magic of Oil Painting guy vs. The Joy of Oil Painting guy
Uhh…
One of those guys is dead right now, so the other guy wins.
Buddy Lee vs The Energizer Bunny
Ummm, it’s The Joy of Painting.
And Bob Ross, (the Joy of Painting guy) wins because he has “happy little trees,” but before he found Christ, he was a serious hellraiser.
That old person smell VS. that new car smell.
Thanks for setting me straight. Who was the old guy with the “mighty trees”? I would think he would win for having more combat-ready trees.
Old person smell NEVER goes away. It wins by endurance.
Mork from Ork vs. ALF
Alf – given how hairy Mork is, he’d assume Mork was a cat and eat him.
The Stones or the Beatles?
Stones, by strength of numbers. Lennon’s dead, McCartney’s too much of a wuss to fight, that leaves just two Beatles.
How about a contest for global domination between two individuals who really, really want it:
The Brain, from Pinky and the Brain
or
Baby Stewie, from Family Guy
The Stones, 'cause Keith is truly a bad motherfucker. Anyone who has done that much heroin and lived cannot be beaten.
Wrigley’s Doublemint gum Vs. Wrigley’s Big Red gum
Energizer Bunny, he beats him like a drum
If Paul wont fight, that only leaves Ringo, as John and George have both passed on.
Stewie gets the early upper hand, as he zaps Brain into ashes. But Brain comes back to try to take over the world the next week, this time by crawling into Stewie’s ear and eating till he hits grey matter.
Big Red passes out as the twins make the blood move to his, uh, big red.
Race Bannon of Johnny Quest vs Racer X of Speed Racer ???
Draw.
Both would end up being gay lovers.
The Bionic Woman vs Seven of Nine
The Bionic Woman was sort of a crybaby if I remember correctly. 7 of 9 can indure that tight uniform she would win.
Yoda vs. Gandalf.
Yoda, because he can channel Fozzie Bear.
Elmer Fudd vs. Yosemite Sam
Yosemite Sam, obviously.
A pineapple vs. a flamingo
Good one! 
I’ll go with a pineapple, as there’s no way a flamingo could swallow it without getting hurt, with all the spikey leaves and stuff.
Two golden tamarin monkeys with pen knives vs. an angry drunk guy from Seattle?
Ultimately, the monkeys with knives.
At first the Drunk will swagger and bellow, tossing and kicking the monkeys around, until one monkey gets in a lucky shot by nicking the drunk’s nut sack. At which point the drunk will end up being flenced within 30 seconds.
John McClane (Die Hard) vs Ash (Evil Dead1,2,& Army of Darkness)
John McClaine, using lighter fluid.
Joan Rivers Vs Shirley McClaine?
Joan, since after all of the plastic surgery, she is more machine then human. Therefore her metal exoskeleton would be impervious to Shirley’s kicks and punches. Then Joan would lean in and rip Shirley’s throat open with her mouth and that would be it.
Axl Rose Vs. Vince Neil
Oh yeah, you aren’t just supposed to say who wins, you are also supposed to say why they would win. That is half the fun of this exercise
Axl, he gave up the hairspray first, and Vince is still overly flamable. One cigarette ash and, “Phoop!” up in flames he goes.
Col. Sanders vs. Foghorn Leghorn
Foghorn Leghorn.
A rooster which regularly beats up on guard dogs can surely beat a dead senior citizen.
Spam vs Hamsters
Spam. It has the backing of the famous Monty Python skit. “Hamster” was only used once in a French taunting.
Archie Bunker vs. Al Bundy