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]

WordNet (r) 3.0 (2006):

winning post
    n 1: the post at the end of a racecourse