The Punisher is decent hand to hand but this is Conan we’re talking about. I’d give him 50/50 odds in hand-to-hand versus a Tyrannosaurus Rex. Castle is going down hard.
The Only Two Lawyers in the Marvel Universe: Matt Murdock vs. Jennifer Walters arguing before the Supreme Court over the SRA (you can decide who has what side)
As for Dr. Wily vs Dr. Eggman (or Robotnik, whichever name you prefer)…
I think it’s pretty clear now that Zero is…
a.) A Wilybot
b.) Responsible for the cataclysm that occurs between classic Megaman and Megaman X
c.) The vector through which Sigma contracts the virus that gives rise to the entire maverick virus of the Megaman X series (presumably, then, Wily created that virus)
Wily’s robots only turn against him to prove themselves better than each other; they won’t hurt him. Wily put together elaborate plans to orchestrate events long after his own death (see MMX5). Wily’s robots (and those of his peers, and their X-era copycats) are capable of further designing and enhancing second and third generation robots. These include robots who cause multiple world-changing cataclysms (The cataclysm, the Eurasia crash, the Omega X’s reploid takeover in the MM Zero series).
Robotnik (Eggman, whatever) Makes some pretty slick stuff, and I’d say he generally seems to roll with a larger army, but he’s never made things that singlehandedly threatened the world (well… maybe the deathegg, if you go by the Archie Comics iteration), and his stuff routinely turns against him and goes all out (Metal Sonic, and if you open the door to Archie, tons of others like Adam and Eve, too). Plus, he’s comedic relief as often as not, nowadays. He genuinely seems like much less of an overall threat.
In a simple fist-fight, Robotnik’s gonna win over old-fogey Wily, but in a contest of robot armies, I think Wily’s got a lock on crazy, blood-thirsty all out warmongering.
I’m holding off on naming a pair cause I like the last poster’s battle of the lawyers match-up
She-Hulk is clearly pro-reg since she was pro-reg in the comics. Murdock would of course go anti-reg. Overall, I’ll go with Murdock in this if She-Hulk is playing it as Walters. Without her jolly green attributes, the sympathy for the blind lawyer (or if you prefer classic rock, sympathy for the devil) wins out.
Battle of the kid sidekicks. Rick Jones vs. Jimmy Olsen.
Battle of the future: Spider Man 2099 vs. Batman Beyond.
Actually she’s suing Stark over it so even though she was for some unfathomable reason pro-Reg during Civil War she isn’t any more. Not that it invalidates your answer. 
Well there’s really no way that Daredevil, with all that he’s gone through when people find out his identity, is going to be pro-reg. I had to make it a vs. battle somehow. 
Wayne Enterprises vs LexCorp
Batman is probably my favorite comic book character of all time, but I hate Batman Beyond. To me Terry is just a whiney little white boy who, by chance of luck, happened to cross paths with an aged Bruce Wayne. While Spiderman 2099 wasn’t a successful concept (like all the 2099, possible short term exception being Doom 2099), it was a* cool * one.
I mean, just look at him, he looks nasty! Compare that to this.
Also, Spiderman 2099 (Miguel O’Hara), was an ethnic character. I don’t know why, but even as a white guy myself this appeals to me as a reader. Spiderman 2099 is stronger, faster, and don’t tell me about Batman’s armor because Spidey’s suped up suit is also elastically armored. He’s a genius, he has claws, and FUCKING VENOM! That’s right, don’t let that guy bite yah.
Batman Beyond just bites the dust.
Still pending: Battle of the kid sidekicks. Rick Jones vs. Jimmy Olsen.
Still pending: Wayne Enterprises vs LexCorp
Mine new: You think the battle of two corporations is big, get a load of this… Darksied and Apokolips vs Age of Apocalypse Earth. Both ruled by wildly powerful despots, both are planets full of warriors, both have internal resistance movements.
Let’s clear these out.
In a straight up boxing match Jones is going to take it; he acted as Bucky for a time and knows moves from Captain America. In a more loose form it’s going to Olsen who can pull more tricks out of his hat than David Copperfield on crystal meth.
I’m not 100% certain of the current status of LexCorp, but with Lex on top it’s going to win. Wayne Enterprises is just a big company while Lex Corp is an engine of evil built around Lex Luthor himself. Since Mr. Wayne only shows up at Wayne Enterprises if he’s needed for a storyline I’m going to say that he doesn’t have the endurance for long term corporate in fighting. The juicy government contracts go to LexCorp.
As for Apokalypse vs. Age of Apocalypse earth I have just two words for you: Omega Effect. Darkseid has the power to kill just about anyone in the universe at his whim. In a top heavy structure like the AoA Earth all he has to do is fire off a blast before he goes to bed and when he wakes up in the morning the seeker beams have caught up with Apocalypse. Then the rest of the world falls into chaos and the New Gods mop things up easily. And that’s assuming he doesn’t have the Anti-Life Equation like the current hints suggest. With the ALE Darkseid doesn’t even fight, he already controls it all.
Ill-tempered World Leaders Fight! Hugo Chavez has begun making public nasty comments about Atlantis and Latveria. Who invades Venezuela first: Dr. Doom or Namor?
Namor. While Doom is spouting off endlessly about his grand plans, noble heritage, and various “yo mamma” insults aimed at Chavex, Namor just yells “Imperius Rex” and trashes the crudler out of Chavez.
Next up: The New Teen Titans vs. the kids from Avengers: The Initiative.
New Titans in a walk. The Avengers kids have some neat powers, no doubt, but the Titans have Robin, Deathstroke’s friggen daughter. and Cyborg. Hell, they have a White Martian and a dude who can jump into your body. Plus way more combat experience. I like the Initiative kids, but they’re toast. Maybe in a few years…
Here’s a fun couple: Mogo, Green Lantern vs. Ego, The Planet With The Porn 'Stache!
I disagree.
Olsen all the way.
He is Mr. Action, & has meta-powers.
Sure, that’s why it’s a two part answer. Standard Bow-Tie Olsen couldn’t fight Rick Jones on his best day and even now probably couldn’t take him in a boxing ring (see this week’s Countdown). On the other hand if you let things get beyond a straight fist fight then Olsen just has too many advantages even if you let Rick have the Nega Bands. What’s Rick going to do against Giant Turtle Boy Olsen?
Sentient planet vs. sentient planet with a Green Lantern power ring? Mogo takes it.
While Mogo vs. Galactus might be an interesting followup bout, I’m going with:
Jesse Custer (bonded with Genesis) vs. Doctor Manhattan.
