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winningest

American  
[win-ing-ist] / ˈwɪn ɪŋ ɪst /

adjective

Informal.
  1. winning win winning most often.

    the winningest coach in college basketball.

  2. most winning or charming.

    the winningest smile in town.


Etymology

Origin of winningest

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

Example Sentences

Examples are provided to illustrate real-world usage of words in context. Any opinions expressed do not reflect the views of Dictionary.com.

Not so for hockey: The bruising tough-guy game is Canadian in origin, and Canada is the winningest team in Olympic history.

From Los Angeles Times

The City Section’s winningest football coach with 300 career wins and a longtime P.E. teacher at Crenshaw High was placed on administrative leave last August on the eve of Crenshaw’s football opener.

From Los Angeles Times

Since then, she has become history’s all-time winningest skier.

From The Wall Street Journal

Benkert, one of the winningest coaches in state history with more than 300 victories, said he’s determined to make it work.

From Los Angeles Times

He was in his second year at the helm of college football’s winningest program, poised to lead Michigan into an upcoming bowl game versus Texas.

From The Wall Street Journal