winning most often: the winningest coach in college basketball.
most winning or charming: the winningest smile in town.
Dictionary.com Unabridged Based on the Random House Unabridged Dictionary, © Random House, Inc. 2023
How to use winningest in a sentence
Problem is, the New England Patriots and Tom Brady—the winningest quarterback in playoff history—are riding into town.Peyton Manning and Tom Brady Don’t Control Their Own Legacies | Evin Demirel | January 18, 2014 | THE DAILY BEAST
Some say it was Eddie Robinson, the winningest coach in NCAA Division I history.Eddie Robinson, College Football’s Winningest Coach | Samuel G. Freedman | August 23, 2013 | THE DAILY BEAST
One of the winningest conservatives in the western world, Australia's John Howard, explains his success controlling firearms.
Every win between 1998 and 2011 vacated, which no longer makes Joe Paterno the winningest coach in college football history.Joe Paterno Was a Dictator: Penn State Deserved Its Punishment | Buzz Bissinger | July 24, 2012 | THE DAILY BEAST
Paterno, the winningest coach in college football history, died on Sunday after a battle with lung cancer.Penn State Coach Joe Paterno Dead at 85: Photos of His Life | The Daily Beast | January 22, 2012 | THE DAILY BEAST
"I'd like to stay the rest of the afternoon, if you don't mind," said Jane, at her winningest.Jane Journeys On | Ruth Comfort Mitchell
Then he turned and looked with the winningest smile at little Raymond.Tom Slade on the River | Percy K. Fitzhugh
"You do not come to see all your friends," she said, with her winningest smile and her most bird-like voice.Gordon Keith | Thomas Nelson Page