winningest
adjective
win·ning·est
ˈwi-niŋ-əst 
: having achieved the most wins
the winningest coach in football
Examples of winningest in a Sentence
She's the winningest coach in the conference.
the winningest team in our school's history
Recent Examples on the Web
Even Tom Brady, the winningest player in NFL history, has wrestled with it.
—
Rustin Dodd, New York Times, 24 Feb. 2026
But there’s no shortage of talent in the program, which hired one of the state’s winningest coaches in Danny Wallace.
—Colby Gordon, Austin American Statesman, 18 Feb. 2026
At the time of her retirement, Vonn was the winningest woman in skiing, with 82 World Cup victories — a record that has since been broken by fellow American Mikaela Shiffrin.
—Rohan Nadkarni, NBC news, 3 Feb. 2026
Already one of the winningest stars of her generation at the Grammys, Gaga has also managed to make herself into a darling of the movie industry.
—Hugh McIntyre, Forbes.com, 21 Jan. 2026
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Rustin Dodd, New York Times, 24 Feb. 2026
But there’s no shortage of talent in the program, which hired one of the state’s winningest coaches in Danny Wallace.
—Colby Gordon, Austin American Statesman, 18 Feb. 2026
At the time of her retirement, Vonn was the winningest woman in skiing, with 82 World Cup victories — a record that has since been broken by fellow American Mikaela Shiffrin.
—Rohan Nadkarni, NBC news, 3 Feb. 2026
Already one of the winningest stars of her generation at the Grammys, Gaga has also managed to make herself into a darling of the movie industry.
—Hugh McIntyre, Forbes.com, 21 Jan. 2026
See All Example Sentences for winningest
Cite this Entry
“Winningest.” Merriam-Webster.com Dictionary, Merriam-Webster, https://www.merriam-webster.com/dictionary/winningest. Accessed 28 Feb. 2026.
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