In the house tom is chasing after jerry like usualy until a sailor in his 40's stops tom in his tracks "What are you doing to that poor innocent mouse cat?" popeye asked tom, tom shruggered "you don't know eh?" popeye cracks his kunckles "time to teach you a lesson cat" tom gets in his fighting stance ready to fight popeye.
i vote inconclusive, both have powers to cancel each other's regeneration out (tom's got sleep manipulation and popeye has transmutation) but it really depends on who hits first, doesnt help that both have insane toon force
In fairness, Popeye is much older than Tom, so he likely has far more experience. I also think that as good as Tom's Toonforce is, Popeye's is stronger. Tom could use his weapons and sleep Manip, though.
Popeye's insta-win moves: Hypnosis, possibly Deconstruction and Transmutation (though Tom's regeneration could negate this.), and just socking Tom out of the cartoon (which is something he can do without spinach.)
Gotta go with the sailor here, I love both characters, but Popeye has way deadlier powers, a better healing factor, and much more experience fighting. Plus, Tom is kinda a coward, so Popeye could just roar at Tom and send him running away screaming...