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4. winningest
to have either the most wins, or the highest win percentage, depending on the sportscaster
Joe Pa will never be this winningest coach no matter how long he's in the game
by BMG Dec 17, 2002 add a video
1. Winningest
An unusual adjective that refers to both the subject and the author simultaneously.

Of the subject: Having the most wins.

Of the author: Being an idiot who can't be bothered to look up a real word.
"Michael Phelps is the winningest athlete in Olympic history"
2. Winningest
This is not a word, though used by some people. As well as explained to be a word Winningest is not a word.
Announcer: That coach is the winningest coach in hockey currently.
Me: Dude, that's not a word.
3. winningest
To have the most wins.
Our coach is the winningest coach is school history.
by anonymous May 9, 2003 add a video
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