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

Nadal is still the winningest player in the history of the French Open, having taken the prize in Paris a record 14 times.

From Salon

Stick is the winningest Football Championship Subdivision quarterback in history with a 49-3 record as a starter at North Dakota State with four FCS national championships.

From Los Angeles Times

With his father on the way to becoming the winningest coach in school history, it seemed inevitable that any future trip to Pasadena would come as part of a package deal.

From Los Angeles Times

A possible postseason preview between baseball’s winningest team and the one that has been playing best in the season’s second half.

From Los Angeles Times

Netflix’s drama “Baby Reindeer” won for limited series, and its creator Richard Gadd won for writing and acting for a total of six awards, making it the third winningest series of the season.

From Los Angeles Times