winningest

[win-ing-ist]
adjective Informal.
1.
winning most often: the winningest coach in college basketball.
2.
most winning or charming: the winningest smile in town.

Origin:
1970–75; winning + -est

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Based on the Random House Dictionary, © Random House, Inc. 2014.
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Example sentences
At press time, they are in a two-way tie for winningest team in the league.
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.
Chop his career in half, and he'd still be both the winningest and second-winningest pro surfer in history.
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