winningest
Americanadjective
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winning most often.
the winningest coach in college basketball.
-
most winning or charming.
the winningest smile in town.
Etymology
Origin of winningest
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.
Looking Wiatt dead in the eye, flashing my winningest smile—
From The Wall Street Journal ● Sep. 15, 2026
Still, the game will have meaning for France since it will be the final match for coach Didier Deschamps, the winningest World Cup manager in history.
From Los Angeles Times ● Jul. 17, 2026
We are the winningest program of 1962 to 2010.
From The Wall Street Journal ● May 7, 2026
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
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
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Get a wordDefinitions and idiom definitions from Dictionary.com Unabridged, based on the Random House Unabridged Dictionary, © Random House, Inc. 2023
Idioms from The American Heritage® Idioms Dictionary copyright © 2002, 2001, 1995 by Houghton Mifflin Harcourt Publishing Company. Published by Houghton Mifflin Harcourt Publishing Company.
