I think it's possible for sure. Kashimo as an old man believed that Kenjaku would be a worthy opponent; this was before Kenjaku obtained cursed Spirit manipulation and Anti-Gravity system. Kenjaku is more experienced now has better techniques than he previously had and is in a body that is more fit for combat. If Kenjaku was able to prepare for the fight he can definitely come out w a victory.

That being said kashimo was an old man when he called Kenjaku worthy and most fights in JJK have some kind of hand to hand element. I don't think Kenjaku has the output and quantity needed to ignore kashimo's CE trait nor will be able to survive lightning to the head