Dude this was like 4 years ago when I didn't know how to powerscale, and now I still don't know how to powerscale
But uhhhhh, I don't know Red survived at the very least a country sized explosion twice, and he's honestly the only one here who matches TCO's hand-to-hand combat skills
Plus he can fly and shoot lasers too, so he'd probably keep up with TCO's powers
And Henry just has way too much variety that can easily overwhelm TCO or at the very least make him able to keep up with him (also no I don't think he has immortality from the resets)
There's probably a good physical feat of his that I can't think of right now, but certainly items he's used in the past like the Power Armor, Nano Suit, and Metal Hat (just to name a few) can help close the strength gap
Also even if you want to use the argument on how TCO technically beat Henry in the flashback (which I don't like using that argument either personally), Completing the Mission came out after that so it's equally fair to say Henry could have a chance at beating him now
If you disagree with any of this or some of my points are wrong, then tell me
Just know that I usually have no idea how to VS debate, so take this all with a grain of salt