winningest

[ win-ing-ist ]

adjectiveInformal.
  1. winning most often: the winningest coach in college basketball.

  2. most winning or charming: the winningest smile in town.

Origin of winningest

1
First recorded in 1970–75; winning + -est1

Dictionary.com Unabridged Based on the Random House Unabridged Dictionary, © Random House, Inc. 2024