Source : Webster's Revised Unabridged Dictionary (1913)

Winning \Win"ning\, 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.

Source : WordNet®

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