Frequency: The word is one of the 3000 most common words in English.
1.
You can use winning to describe a person or thing that wins something such as a competition, game, or election.
...the leader of the winning party...
Donovan scored the winning goal.
ADJ: ADJ n
2.
You can use winning to describe actions or qualities that please other people and make them feel friendly towards you.
She gave him another of her winning smiles...
= engaging
ADJ: ADJ n
3.