Etymology
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winning (n.)

"thing gained or won," late 14c., verbal noun from win (v.). Related: Winnings.

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Definitions of winning
1
winning (adj.)
having won;
the winning team
Synonyms: victorious
winning (adj.)
very attractive; capturing interest;
a winning personality
Synonyms: fetching / taking
2
winning (n.)
succeeding with great difficulty;
winning is not everything
From wordnet.princeton.edu