winningest
Americanadjective
-
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
Reeve and Cunningham were seen speaking before the game, but the WNBA’s all-time winningest coach declined to reveal the details of their discussion to reporters afterward.
From Los Angeles Times ● Aug. 3, 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
We are the winningest program of 1962 to 2010.
From The Wall Street Journal ● May 7, 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.
