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Yes, Ladies, Gentlemen, and Otherkin, it's time for The game where you pit two worthy rivals against each other, describe the conflict (without being any more verbose or complicated than absolutely necessary, please), and leave it to the next poster to say who wins and why/how (once again, no more verbose than about two lines at most)! Also, while individual characters may be brought out multiple times, let's please agree not to pit the same duo against each other more than once, even with different circumstances of conflict.
I'll start with the Big Question to get it out of the way:
For the next poster's consideration:
a South American bird-eating spider VS Thing Addams - who wins in a one-on-one to-the-death cage match?
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Spider. Spiders always win. Lolth would take away my powers if I said otherwise.
Poker.
Han Solo vs James Bond
We all know Han shot first. Han shoots Bond for the win before the first hand is even done.
Godzilla vs Gamera. FIGHT!
Only one of those groups can collectively be considered "Good Boys." The dogs win it.
Who wins in a race over hot coals - a troll or a treant?
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Troll. 24 hours later, the treant is still trying to say "May the best being win"
An average goblin versus a forum troll in A causing the most havoc competition.
The goblin, quite willing to do literal violence and heap physical abuse, makes lengthy sport of the internet troll.
Don Juan vs. Don Ameche.
All Juan has to do his perform his patented swagger, raise an eyebrow, and Ameche would be putty in his hands.
An Ancient Dragon vs. an Elven Lich in a "Who has the coolest-looking lair" competition.
Dragons have good taste in hoards, and elves just like trees and stuff anyway.
Rovagug vs Cthulu
Cthulhu don't take no lip from no chaos lap dog. The Big C wins easy peasy.
An awakened catoblepas vs a stone giant lord in a double dutch contest.
Stone giant lords can have the stone giant priests cast spells on them to help. Thus, I'm giving it to the stone giant.
Iphone vs Blackberry in a pie eating contest.
Blackberry.Because that pie ain't apple.
Siri vs Cortana in a weight-lifting competition.
Well, since prostitutes don't count... it's a tie.
Unarmed level 1 commoner vs. declawed housecat in a duel to the death.
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"Declawed" being one of the crueler Curses for Housecat Oracles, the cat makes judicious use of his spectacular Stealth score execute hit-and-run tactics as he inflict light wounds the Commoner to death.
Count Dracula (Original-Castlevania version) VS The Phantom of the Opera (badass live-on-Broadway version): The Phantom is exploring Castlevania for reasons of his own while the Belmonts are all on vacation or something and Alucard has gone off to try his hand at being this decade's "rich-foreign-noble-party-animal" at UC Santa Barbara. Will Castlevania entomb the Phantom like so many hapless adventurers before him, or might Dracula wake up to discover that some strange new "ghost" has proved himself better at haunting a magical trap-laden castle than the Count ever was?
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The Phantom, without breaking a sweat. Broadway Phantom is based on the original, who was an expert trap-builder. Dracula didn't recognize his own security consultant.
Tarrasque vs Barney, the purple dinosaur you love and who loves you and you're a happy family.
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Given that you failed to stipulate the nature of their duel, I will take the reasonable liberty of assuming it's a "Who's more Evil?" contest - in which case, Barney wins hands down, as he has been an accessory to real-world torture.
Jessica Rabbit VS 7 of 9 - Unleashed on the Real World, who manages to seduce their way to world domination first (also fully in play are Jessica's Toon abilities and 7's Borg abilities)?
7 of 9. Borg + internet = everyone is implanted with robot eyes.
Who would in a battle of being the most hated character in fiction: Joffrey Baratheon or Dolores Umbridge?
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Must be Dolores Umbridge, since I don't know anything about the other one (aside from guessing he's a George R. R. Martin character) and nobody else hated him enough to say otherwise.
The Titanic from Dr. Who Christmas special "Voyage of the Damned" VS the Titanic from Futurama episode "A Flight to Remember" - The Doctor determines that, by going back and warning himself to never board the one, and cosmology-hopping to the Futurama universe to prevent the Planet Express team from ever boarding the other, he will, by thereby preventing a certain unknowable precise sequence of events, manage to save ONE of the otherwise-doomed vessels...but only one. Which one is otherwise most likely to make it?
Lucy of course. Lucy has the power to perfectly mimic Wonka's every move as well as incomparable grape stomping skills. She is clearly more powerful in this situation.
Some kind of supernatural beastie has been murdering innocent people, and both Harry Dresden and John Constantine are called in to investigate. Who apprehends the murderer first?
Harry. Constantine is the one who sets it up, but he'd rather that nobody on the supernatural scene knows he was involved.
Achilles or Hector?
Hector for the win! Even though Hector was killed by Achilles, Hector killed 31,000 men. It was a light Tuesday for Hector.
Ford vs. Chevy: Who can rust the fastest?
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Chevy, clearly. His career's been a mean punchline for decades now, while Ford is getting ready to once again take up the hat and bullwhip!
Ozymandias VS Codename 'V': Can V manage to hunt down and assassinate all the plutocrats, hatemongers, war criminals, political theocrats, police state apparatchiks, and ecomurderers who have collaboratively ruined the 21st Century, yet all remain conspicuously-untouched thus far, before their combined blundering leads the world all the way up to 12:00 on the Doomsday Clock...or will Ozymandias need to step in and save the world 35 minutes ago?
V.
Knowing of Ozymandias' physical prowess, V would instead attack his legacy: his assets. His buildings and factories. His charitable foundations. V. would lay Ozy's sins bare before the world, and the blow up the building he was in. O. would die, but only after knowing that he would be remembered as just another wealthy man with delusions of grandeur.
Superman vs Captain Marvel (DC version)
Superman.
Superman would call Batman, get Captain Marvel's weakness, and then execute a more heroic version of whatever plan Batman comes up with. Because Batman knows everything.
Batman vs. Evil Batman
Match. Despite his protestations to the contrary, Batman is actually quite amoral. He regularly commits crimes in order to fight crime, including criminal trespassing, theft, kidnapping, intimidation, and physical assault (of people who are not immediately threatening).
His code against killing? How many innocent people have been killed by the Joker/Killer Croc/Zsasz when they escape from Arkham because Batman refuses to kill them?
And why? Because if you kill a killer you become like them? That isn't true of the police, who Batman works with and respects. Because it would taint public perception of Superheroes? As if Batman could not make a killer disappear without a trace, and as if anyone would come looking for them.
In truth, Batman's arbitrary code of conduct is more important to him than the lives of the people of Gotham. His obsession is not with ending crime in Gotham. If it was, he would use his wealth and influence to incite urban renewal, lowering poverty, increasing employment, and enforcing police presence in low income areas, all of which would go much further to reduce crime than beating people up. The billion dollars he spends on a bat themed supersonic jet would go much farther in the Gotham public educational system, and do much more good.
Batman is not interested in ending crime, but in fighting crime. Acts of violence and self harm to satisfy his emotional turmoil that do nothing to solve the overarching problems or protect people, because he doesn't -want- crime to end. He wants to hit people and be hit.
If that's the "good" Batman, what does the evil one look like? The same, but with a goatee?
By the way, Captain Marvel doesn't really have a weakness, other than sharing a name with DC's primary competitor, which keeps them from making him a mainstream hero. Even his childish naivete is balanced by the Wisdom of Solomon. He is a physical match for Superman, uses magic (which is one of Superman's weaknesses), and his comic was actually more powerful than Superman during the 40's and 50's.
So.
Fear of Spiders vs Fear of Clowns
Fear of spiders of course. I mean, clowns have their own organizations full of people! They have fun and they do a lot of charity (oh shoot, my union fees are due). You don't often see people signing up to sit in a funnel web spider's, uh, funnel web. People rarely check under the toilet seat for clowns. People also don't keep a bottle of clown-antidote handy. It's just always going to be spiders...slowly crawling towards you...slick, dark, ominous...each with a poison that shouldn't be allowed to kill something 70,000 times its body weight. Sweet dreams.
Sticking with my vehicle theme: Optimus Prime or Stephen King's Christine - which one wins as the best 'prom date' vehicle?
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I'm no true expert on either, but given that I think the primary purpose of prom date vehicles is post-prom/pre-prom/heck, during-prom snu-snu, and my having repeatedly been informed that Optimus Prime was a quintessential Paladin, I'm going to conclude that Christine wins this:
Optimus Prime would (not necessarily in sequence) observe with keen befuddled interest, strafe the daters with question after thoroughly-mood-killing question, politely but repeatedly ask you to "please remember to clean that up as soon as your biomechanical gestalting sequence has completed", and whether you are "absolutely CERTAIN you do not require prompt and thorough reapplication of sealant? You both appear to be leaking an extensive array of oils, antifreeze, and assorted heavy lubricants at a worrisome rate, and under an even more worrisome force of pressure!", and repeatedly offering to contact both your parental units.
Christine, on the other hand, would also observe with keen interest, but so long as neither of you were so thoughtless as to cross in front of her headlights after exiting, otherwise would restrict her activities to semi-obscene grunts and growls of approval from her engine, the occasional highly-stimulating jolt from her hydraulics, airbag-spanking, and spontaneously activating the radio and turning it to either the mood-elevating ruckus of the local black metal station, the sinister yet beatific splendor of the local "All Russian Composers" classical station, the local NPR station featuring the rough, smoky sensuality of Amy Goodman, or the absolute, frenzy-inducing kink-factor of the local televangelical dashboard-Jesus station.
Cmdr. Saru (Star Trek: Discovery) VS Puddleglum the Marsh-Wiggle (The Chronicles of Narnia): After a crazy transcosmological mix-up caused when Lt. Cmdr. Stamets gets into the "Angry Tardigrade Black-Label Black-Alert Red-Star Funky-Action-At-A-Distance Top-Shelf Reserve", our two not-at-all-ever-glad-iators find themselves trapped in each others' worlds, with each others' companions, having just embarked upon each others' great and terrible adventures.
Who manages to prevail in the others' inhumanly tight pointy shoes, perhaps even outperforming the other in his own quest...and who dooms, glooms, and generally buzzkills his new 'friends' to the point of dragging them all down until they are all too eager to willingly throw themselves into the jaws death and defeat?
Note that those two fates need not strictly be mutually exclusive....