Well I am not sure if this is just Iron Man in his regular armor, or if he can change his armor and wear the Hulkbuster Armor so I am a bit hesitant to answer without knowing which.
But If it's the latter, I see no reason why Iron Man couldn't just wear his own Hulkbuster Armor and then use his technopathy powers to remotely control one or more Hulkbuster Armors and various other armors to take on Pitt while staying at a safe distance away.
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Well with the rules of the fights it is the current incarnation of the character so that wouldn’t include the Hulkbuster armor. Does the Hulkbuster armor have the same shield protection as the current version? If so that would be a major change in the fight, if Pitt’s claws can’t get to him then I can’t see much that Pitt can do.
Not sure about the shields, but I think that'd be a moot point against Pitt. To me, an onslaught of punches from WWH is far superior to anything Pitt and his claws can dish out. *shrugs*
Now the Hulkbuster was taking said punches for quite a while, whilst smacking up Hulk in the process. Granted, Tony was eventually beaten, [just like everyone else], but he did better than most others against WWH.
Well, I'm not going to argue what Pitt's claws and what they can cut through (I don't know Pitt well enough), but Tony Stark did design and build an adamantium Iron Man Armor. I'm sure that would stand up to Pitt's claws.
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There is a big difference though when delivering a large force over a larger area (Hulk’s Fists) then a large force over a smaller area (Pitt’s Claws), you would need less force to puncture through something such as his armor. His claws would act more like armor piercing then a concussive force such as Pitt, now I would agree that Hulks punch have much more concussive force than Pitt’s punches.
It's too bad that Tony had those nanities he was going to use on WWH were messed with before he got to use them. Because odds are more than likely it would have put WWH down.
But none the less Tony's satellite ray did the job anyway I guess later on.
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Nothing that I have ever seen has broken one of his talons, he has ripped through Creed armor and ship hulls like they were nothing, dug through solid rock faster than people can walk.
This thread isn't h2h or slug fest only. Tony could if he chose to could go h2h but, that's not where he's going to be utilizing his shizznit. Periodic close quarters combined with repulsors, sonics, force fields, lasers, missles, technopathy with other suits other weapons...etc. Pitt would get overloaded with Tony's arsenal and fists.
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I highly doubt that, Pitt has went against entire platoons of Creed warriors all armed to the teeth and wiped them out, against Creed bounty hunters created just to take him out. The weapons on his suit wouldn’t do much other than tick him off, the force field may hold him back and I’m not sure about this technopathy thing but Pitt also possesses limited telepathy himself.
Now I will agreed that I do not know all there is about IM but from what I have seen his basic suit will not take down Pitt by any means, the shield may hold him off but I can not see him stopping him. The Hulkbuster would do more in combination with the shields but Pitt is far faster then Hulk and more savage to boot.
There isn't much of a chance that Ironman would win against Pitt, when was the last time Ironman defeated hundreds or perhaps thousands of alien beings that were on par or greater in power than the Thing?
Pitt was bio engineered to destroy entire worlds filled with super powered beings, he also defeated a cosmic aberration named Urgrul Thul, who on panel was stated to be able to kill Gods and rape Angels... Ironman is just not on the level. For example we all saw what Thor did to him, even classic Thor had the power to destroy Ironman.
Caitlin Fairchild was barely able to hold Pitt at bay, and he wasn't really trying to kill her, Caitlin is stated to be on Supergirls level in strength and durability. There is no way on earth that Ironman is on Gladiators level or a Kryptonian. Without mind games Sentry would have ripped him out of his suit.
Pitt stopped Supreme and nearly killed him when he thought that Supreme was another bounty hunter that was after his head, and he had Image comics Thor's hammer to boot. Supreme is above Gladiator, who is above Ironman.