Winning means charming and likeable — or simply coming first. Two senses that sit oddly together.
The competitive sense is the obvious one, so a winning goal, the winning ticket and a winning streak all mean victory. The charm sense is older and gentler, and a winning smile is one that wins people over rather than a contest. It is nearly always used of a smile or a manner. The noun winnings means the money you have won, and it is always plural.
1adjectivewinningCharming and appealing.~2%
“He has a winning way with customers.”
2adjectivewinsThat wins, or has won.~98%
“She scored the winning goal in the last minute.”
Shares are an estimate: a language model read 26 sentences found in the wild and placed 8 of them on a sense (18 were unclear) — a count of our sample, not a measurement of English.