Webster's Revised Unabridged Dictionary · 1913

Winning

Winning , adjective

Attracting; adapted to gain favor; charming; as, a winning address.
Each mild and winning note. — Keble

Winning , noun

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.
(a) (Mining) A new opening.
(b)
(Mining) The portion of a coal field out for working.
Collocations (2)
Winning headway (Mining) , an excavation for exploration, in post-and-stall working.
Winning post , the post, or goal, at the end of a race.