winningest

[ win-ing-ist ]

/ ˈwɪn ɪŋ ɪst /

winning most often: the winningest coach in college basketball.

most winning or charming: the winningest smile in town.

Origin of winningest

First recorded in 1970–75; winning + -est¹

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 |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 |DAILY BEAST
One of the winningest conservatives in the western world, Australia's John Howard, explains his success controlling firearms.

Australia's Example for Controlling Guns |David Frum |January 17, 2013 |DAILY BEAST
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 |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 |DAILY BEAST
Then he turned and looked with the winningest smile at little Raymond.

Tom Slade on the River |Percy K. Fitzhugh
"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
"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