Dictionary.com
Thesaurus.com

winningest

American  
[win-ing-ist] / ˈwɪn ɪŋ ɪst /

adjective

Informal.

  1. winning most often.

    the winningest coach in college basketball.

  2. most winning or charming.

    the winningest smile in town.

Etymology

Origin of winningest

First recorded in 1970–75; winning + -est 1

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

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

When I went to Big Creek, Coach Merrill Gainer, the winningest coach in southern West Virginia history, took one look at me lost inside the practice gear and ordered me off his football field.

From "October Sky" by Homer Hickam

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.