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[win-ing-ist] /ˈwɪn ɪŋ ɪst/
adjective, Informal.
winning most often:
the winningest coach in college basketball.
most winning or charming:
the winningest smile in town.
Origin of winningest
1970-75; winning + -est1 Unabridged
Based on the Random House Dictionary, © Random House, Inc. 2015.
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Examples from the Web for winningest
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  • Then he turned and looked with the winningest smile at little Raymond.

    Tom Slade on the River Percy K. Fitzhugh
  • "I'd like to stay the rest of the afternoon, if you don't mind," said Jane, at her winningest.

    Jane Journeys On Ruth Comfort Mitchell
  • "You do not come to see all your friends," she said, with her winningest smile and her most bird-like voice.

    Gordon Keith Thomas Nelson Page

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