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two of the most powerful Marvel heels ... who wins this one ?

Gladiator already handled Juggie in one of the x-men series. Only way jugs can win is if he finds a way to lower Glads confidence, if he doesn't then jugs is toast. Glads is kind of like the Hulk meaning that when you get the hulk angry he gets stronger and his Glads confidence keeps getting stronger, he's pretty much a powerhouse to stop.

he said classic

Doesn't it make sense that someone who has a stationary level of invulnerability like Juggernaut would be less inv. than someone like Gladiator whos inv. is leveled to existence.

I say Glads. Wouldn't be easy though...

Stalemate. This might as well be Hulk vs. Juggernaut.

If I may quote long pig (not verbatim): "Juggernaut can stalemate any version of the Hulk. And, if given enough time, can beat them all".

The same really applies here. If given enough time, Juggernaut will EVENTUALLY defeat Glads.