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winningest

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

adjective

Informal.
  1. 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.

Hall of Fame high school football coach Bob Johnson, who turned El Toro and Mission Viejo into powerhouse high school football programs and became one of the winningest coaches in state history, has died.

From Los Angeles Times • Mar. 11, 2026

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

From The Wall Street Journal • Feb. 5, 2026

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 • Dec. 13, 2025

Donahue remains the winningest coach in Pac-10 Conference history with 151 victories.

From Los Angeles Times • Dec. 7, 2025

When I went to Big Creek, Coach Merrill Gainer, the winningest coach in southern West Virginia history, took one look at me lost inside the practice gear and ordered me off his football field.

From "October Sky" by Homer Hickam