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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.

winningest 

To have the most wins.
Our coach is the winningest coach is school history.
winningest by Anonymous May 9, 2003

Winningest 

Winningest is an adjective invented by loudmouth sports fans used to brag about their team’s past record. It is used to reflect their team’s past victories to deflect from their team’s current failures.

Nobody says a team is the ‘winningest’ unless their recent statistics are laden with failure.
The University Of Michigan is the winningest team in college football! (They haven’t won squat in 2 decades)

We have the winningest team in history! (Going back to when there were only a handful of teams & blacks weren’t allowed to play yet)
Winningest by Cellblockearth October 17, 2021

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
winningest by BMG December 17, 2002

split the winnings 

To halt the laying of a cable halfway through.
"And after four days without movement, Job took up his toilet and great was his relief. But even as he released his burden there came a voice and it was the Lord. And the Lord spoke in a loud voice saying Come unto Me Job. And Job replied saying Oh God, what is it this time, for I have only just sat down. And great was the wrath of the Lord. And He commanded Job to split the winnings and come now unto Him. And great was Job's discomfort. (from 'The Book of Job',Ch.9)

windigestion

Windigestion is when you have indigestion coupled with a bit of trapped wind, hence windigestion. It can be quite painful!
I should never have had those beans on toast tonight after that huge meal I had for lunch, now I've got a case of really bad windigestion.
windigestion by Lizzie the Frog October 9, 2008