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4.
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 December 17, 2002
 
1.
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"
by Tom2003 August 20, 2008
 
2.
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.
by Spelling Nazi misspellings die December 31, 2010
 
3.
To have the most wins.
Our coach is the winningest coach is school history.
by Anonymous May 09, 2003