/ Dictionary / Index W winningest: Meaning and Definition of Find definitions for: win•ning•est Pronunciation: (win'ing-ist), [key] — adj. Informal. winning most often: the winningest coach in college basketball. most winning or charming: the winningest smile in town. Random House Unabridged Dictionary, Copyright © 1997, by Random House, Inc., on Infoplease. See also: winningest (Thesaurus) winning winning gallery Related Content Daily Word Quiz: tactful Analogy of the Day: Today’s Analogy Spelling Bee: Today’s Spelling Bee Frequently Misspelled Words Frequently Mispronounced Words Easily Confused Words Writing & Language