winningest
Americanadjective
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winning most often.
the winningest coach in college basketball.
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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.
Minnesota Lynx’s Cheryl Reeve became the WNBA’s all-time winningest coach Wednesday, earning her 380th victory and surpassing close friend and colleague Mike Thibault.
From Los Angeles Times ● Jul. 11, 2026
“For me, never is this a red card,” said Pochettino, now the winningest U.S. coach in World Cup history.
From Los Angeles Times ● Jul. 2, 2026
Alston, who managed the team’s final four seasons in Brooklyn, is the team’s winningest manager and won four of the franchise’s nine World Series titles, the first coming in 1955.
From Los Angeles Times ● Jul. 1, 2026
Fluky bounces can swing series and the winningest teams from the regular season can just as easily get swept in the first round as the wild card clubs.
From The Wall Street Journal ● Jun. 15, 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
Definitions 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.
