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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.

Courteney, one national victory away from becoming the winningest coach in history, is not ready to quit.

From Los Angeles Times

They formulated an identity, and rode it to the winningest season in their franchise’s history at 97-65.

From Los Angeles Times

He’s at 295 career wins, the winningest coach in City Section history.

From Los Angeles Times

The Dodgers entered their weekend series with the Angels as the winningest team in the National League.

From Los Angeles Times

Kling, who lost his home in the Palisades fire, is the winningest high school tennis coach in state history, having amassed more than 1,440 victories.

From Los Angeles Times