ANSWERS: 1
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An older form of "will" is "woll." So "won't" came from "woll not," just like "shouldn't" came from "should not." As far as "willn't" goes, the Oxford English Dictionary quotes Charlotte Bronte as writing "That willn't wash miss.' in 1849. So I guess it HAS been used. But it sure is harder to say than "won't."
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