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Meaning of winningest

win•ning•est

Pronunciation: (win'ing-ist), [key]
— adj. Informal.
  1. winning most often: the winningest coach in college basketball.
  2. most winning or charming: the winningest smile in town.
Random House Unabridged Dictionary, Copyright © 1997, by Random House, Inc., on Infoplease.
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