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winningest

[win-ing-ist]
adjective Informal.
  1. winning most often: the winningest coach in college basketball.
  2. most winning or charming: the winningest smile in town.
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Origin of winningest

First recorded in 1970–75; winning + -est1
Dictionary.com Unabridged Based on the Random House Unabridged Dictionary, © Random House, Inc. 2018

Examples from the Web for winningest

Contemporary Examples of winningest

Historical Examples of winningest

  • "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

  • Then he turned and looked with the winningest smile at little Raymond.

    Tom Slade on the River

    Percy K. Fitzhugh

  • "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