"winning" in the noun sense
1. winning
succeeding with great difficulty
"winning is not everything"
"winning" in the verb sense
1. win
be the winner in a contest or competition be victorious
"He won the Gold Medal in skating"
"Our home team won"
"Win the game"
2. acquire, win, gain
win something through one's efforts
"I acquired a passing knowledge of Chinese"
"Gain an understanding of international finance"
"win someone's confidence and friendship"
3. gain, advance, win, pull ahead, make headway, get ahead, gain ground
obtain advantages, such as points, etc.
"The home team was gaining ground"
"After defeating the Knicks, the Blazers pulled ahead of the Lakers in the battle for the number-one playoff berth in the Western Conference"
"win points"
4. succeed, win, come through, bring home the bacon, deliver the goods
attain success or reach a desired goal
"The enterprise succeeded"
"We succeeded in getting tickets to the show"
"she struggled to overcome her handicap and won"
5. earn, garner, win
acquire or deserve by one's efforts or actions
"its beauty won Paris the name 'City of Lights'"
"winning" in the adjective sense
1. victorious, winning
having won
"the victorious entry"
"the winning team"
2. fetching, taking, winning
very attractive capturing interest
"a fetching new hairstyle"
"something inexpressibly taking in his manner"
"a winning personality"
Source: WordNet® (An amazing lexical database of English)
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