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.
That earned them a fifth straight trip to the playoffs and a first-round meeting with the Colorado Avalanche, the league’s winningest team, beginning Sunday in Denver.
From Los Angeles Times • Apr. 17, 2026
Since then, she has become history’s all-time winningest skier.
From The Wall Street Journal • Feb. 5, 2026
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 • Dec. 13, 2025
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
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.
