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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.

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

With 35 trophies to her name, the pop superstar is the winningest artist in the nearly seven-decade history of music’s most prestigious awards show; with 99 nods, she’s the most-nominated act of all time too.

From Los Angeles Times

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