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Well, Winnie-the-Pooh has the initial advantage because he has back legs, whereas Sooty just has a hand up his backside. However, Winnie-the-Pooh is only stuffed with stuffing, whereas Sooty contains a large fist - significantly more powerful than teddy-bear stuffing and capable of punching red-shirted bears hard on the nose.
Then again, Sooty doesn't have a mouth (or if he does, it's stitched up), whereas Winnie-the-Pooh does, and it is presumably filled with hugeawesome bear teeth that could rip Sooty (and the hand inside him) apart in seconds.
But then, Sooty is a magician and has all the powers of the Dark Arts at his beck and call, so I'm inclined to think he'd use his evil powers to simply disintegrate Winnie-the-Pooh and have done with it.
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