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From The Collaborative International Dictionary of English v.0.48:
Winning \Win"ning\, n. 1. The act of obtaining something, as in a contest or by competition. [1913 Webster] 2. The money, etc., gained by success in competition or contest, esp, in gambling; -- usually in the plural. [1913 Webster] Ye seek land and sea for your winnings. --Chaucer. [1913 Webster] 3. (Mining) (a) A new opening. (b) The portion of a coal field out for working. [1913 Webster] Winning headway (Mining), an excavation for exploration, in post-and-stall working. Winning post, the post, or goal, at the end of a race. [1913 Webster]