It does matter which version of which, really. I do believe it could go either way between Savage Hulk and DOS Doomsday and Savage can pull off the majority against Doomsday Rex.
Current "Planet Hulk" version of Hulk would lose to all of them, though.
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He's not gonna kill an angry classic Savage Hulk. That's not gonna happen. He may be able to hurt and possibly kill Tales To Astonish Savage Hulk, but eighties Savage Hulk and Mindless Hulk are not going to get killed by him. However, Doomsday does have the speed advantage + he still can evolve, so he'll probably kick him around.