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[win-ing-ist] /ˈwɪn ɪŋ ɪst/
adjective, Informal.
winning most often:
the winningest coach in college basketball.
most winning or charming:
the winningest smile in town.
Origin of winningest
1970-75; winning + -est Unabridged
Based on the Random House Dictionary, © Random House, Inc. 2015.
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Examples from the web for winningest
  • At press time, they are in a two-way tie for winningest team in the league.
  • Chop his career in half, and he'd still be both the winningest and second-winningest pro surfer in history.
  • Two weeks earlier, he had become the winningest coach in the history of college basketball.
  • The all-time winningest motocross rider's crash course in stock cars continued recently with a crash.

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