winningest

[ win-ing-ist ]
/ ˈwɪn ɪŋ ɪst /
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adjective Informal.

winning most often: the winningest coach in college basketball.
most winning or charming: the winningest smile in town.

Origin of winningest

First recorded in 1970–75; winning + -est1
Dictionary.com Unabridged Based on the Random House Unabridged Dictionary, © Random House, Inc. 2019

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