Win some or win some ( two words ) means to gain the prize; to come in first, as in a race; or to gain the victory ( win ); in part, or part of the time ( some ) --
He hopes to win some money in the sweepstakes.
Oh, well--you win some; you lose some.
Winsome or winsome ( one word ) means charming or beguiling--
She batted her eyes and gave him a winsome smile.
That child has a winsome manner, and always seems to get her way.
Now that you know that, you can say--
"She was at her winsome best when she asked the judge if he thought she might win some of the prizes."
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