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.
Not so for hockey: The bruising tough-guy game is Canadian in origin, and Canada is the winningest team in Olympic history.
From Los Angeles Times • Feb. 27, 2026
The Vikings knocked off Troy and the winningest coach in California history, Kevin Kiernan, in the quarterfinals.
From Los Angeles Times • Feb. 20, 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
The hardship paid off for Irwin, who became the winningest trainer in the nation, but it took a toll on the animals.
From "Seabiscuit: An American Legend" by Laura Hillenbrand
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.
