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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"
Winningest by Tom2003 October 14, 2008

Winning Smile Day 

January 21st, the day where everyone if not all will wear the ROBLOX accessory Winning Smile.
Winning Smile Day by Fascist Face December 13, 2020

tri-winning 

awesomeness that transcends beyond even Charlie Sheen's level.
Guy 1: "Charlie Sheen may be bi-winning, but I'm tri-winning!"
Guy 2: "What did you do?"
Guy 1: "I raced a dozen cop cars and won!"
Guy 2: "Thuggin'!"
tri-winning by Da Sperminator June 18, 2011

Are ye winning son? 

are ye winning son?yes, father, I am winning, I am playing Minecraft so I am obviously winning thanks for checking on me even if you don't understand those words really encouraged me now I am gonna win, Father I died the creepers killed me :(, father I am playing overwatch wish me luck, father I died, father, I bought something using your credit card I hope that is ok with you
1) The constant state of winning.
2) To one up Charlie Sheen.
1) Five, four, three, two... Wunning!
2) Man, Mayor Moon was wunning all over the place during the campaign rally.
Wunning by Kombo July 30, 2011
“I'm Not Bipolar, But Bi-Winning”

"Well, I mean, first of all come Wednesday morning they’re gonna rename it Charlie Bros. and not Warner Bros. Duh, winning! It’s, like, guys, IMDB right there, 62 movies and a ton of success. I mean, c’mon bro, I won best picture at 20. I wasn’t even trying. I wasn’t even warm."

""I have cleansed myself. I closed my eyes and in a nanosecond, I cured myself... It's the work of sissies. The only thing I'm addicted to is winning. "

“Winning, anyone? Rhymes with winning. Anyone? Yeah, that would be us. Sorry, man, didn’t make the rules. Oops!”

“I’m so tired of pretending my life isn’t perfect and bitching and just winning every second and I’m not perfect and bitchin’.”

“Oh wait, can’t process it. Losers. Winning. Buh bye.”
Winning by kboogie77 March 15, 2011