Possible Definitions:
1. Winning (a.) Attracting; adapted to gain favor; charming; as, a winning address.
2. Winning (n.) The act of obtaining something, as in a contest or by competition.
3. Winning (n.) The money, etc., gained by success in competition or contest, esp, in gambling; -- usually in the plural.
4. Winning (n.) A new opening.
5. Winning (n.) The portion of a coal field out for working.