Winning, a.
Attracting; adapted to gain favor; charming; as, a winning address. "Each mild and winning note." Keble.
1 other Webster entry under this spelling
Winning, n.
1. The act of obtaining something, as in a contest or by competition.
2. The money, etc., gained by success in competition or contest, esp, in gambling; -- usually in the plural. Ye seek land and sea for your winnings. Chaucer.
3. (Mining) (a) A new opening. (b) The portion of a coal field out for working. Winning headway (Mining), an excavation for exploration, in post-and-stall working. -- Winning post, the post, or goal, at the end of a race.
Shades of meaning
Fernald has no entry of its own for winning; he lists it under amiable, charming.
Where he writes about it:
To tempt is to endeavor to lead one wrong; to seduce is to succeed in winning one from good to ill. — from allure
The engaging, winning, and winsome add to amiability something of beauty, accomplishments, and grace. — from amiable