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.
The City Section lost its most experienced and winningest coach, Robert Garrett, who left Crenshaw in March after being reassigned.
From Los Angeles Times ● Jul. 26, 2026
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
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
The winningest superstar played like he had everything to lose.
From Los Angeles Times ● May 2, 2026
In math class he made a pie chart of the winningest World Cup jersey numbers of the past fifty years.
From "Booked" by Kwame Alexander
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.
