winningest

[ win-ing-ist ]

adjective

, Informal.

1. winning win winning most often:

   the winningest coach in college basketball.

2. most winning or charming:

   the winningest smile in town.

Word History and Origins

Origin of winningest¹

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

Example Sentences

Problem is, the New England Patriots and Tom Brady—the winningest quarterback in playoff history—are riding into town.

From The Daily Beast

Some say it was Eddie Robinson, the winningest coach in NCAA Division I history.

From The Daily Beast

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

From The Daily Beast

Every win between 1998 and 2011 vacated, which no longer makes Joe Paterno the winningest coach in college football history.

From The Daily Beast

Paterno, the winningest coach in college football history, died on Sunday after a battle with lung cancer.

From The Daily Beast

"I'd like to stay the rest of the afternoon, if you don't mind," said Jane, at her winningest.

From Project Gutenberg

Then he turned and looked with the winningest smile at little Raymond.

From Project Gutenberg

"You do not come to see all your friends," she said, with her winningest smile and her most bird-like voice.

From Project Gutenberg