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now that I think about it you are right. I don't think there was really a one-on-one confrontation between old toon Raphael and Shredder. Raphael in the new toon didn't even get a character centric one shot episode in season three like the other turtles did. Its not till sseasons four and five that Raphael gets any character centric episodes.
However he does have some interaction with other villans in later seasons, and even in season three Raphael was the one that came up with the plan to defeat Rat King and Leatherhead by gettting them to blow-up the truck load of poisen that Rat King had stolen, in the episode Leatherhead Meets the Rat king. So that sort of makes him the hero in that episode since he came up with the plan that defeated them.
but you are right, Raphael didn't have any one-on-one battles with Shredder that i can think of in the old toon.
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