Source : Webster's Revised Unabridged Dictionary (1913)

Win \Win\, v. t. [imp. & p. p. {Won}, Obs. {Wan}; p. pr. & vb.
   n. {Winning}.] [OE. winnen, AS. winnan to strive, labor,
   fight, endure; akin to OFries. winna, OS. winnan, D. winnen
   to win, gain, G. gewinnen, OHG. winnan to strive, struggle,
   Icel. vinna to labor, suffer, win, Dan. vinde to win, Sw.
   vinna, Goth. winnan to suffer, Skr. van to wish, get, gain,
   conquer. [root]138. Cf. {Venerate}, {Winsome}, {Wish},
   {Wont}, a.]
   1. To gain by superiority in competition or contest; to
      obtain by victory over competitors or rivals; as, to win
      the prize in a gate; to win money; to win a battle, or to
      win a country. ``This city for to win.'' --Chaucer. ``Who
      thus shall Canaan win.'' --Milton.

            Thy well-breathed horse Impels the flying car, and
            wins the course.                      --Dryden.

   2. To allure to kindness; to bring to compliance; to gain or
      obtain, as by solicitation or courtship.

            Thy virtue wan me; with virtue preserve me. --Sir P.
                                                  Sidney.

            She is a woman; therefore to be won.  --Shak.

   3. To gain over to one's side or party; to obtain the favor,
      friendship, or support of; to render friendly or
      approving; as, to win an enemy; to win a jury.

   4. To come to by toil or effort; to reach; to overtake.
      [Archaic]

            Even in the porch he him did win.     --Spenser.

            And when the stony path began, By which the naked
            peak they wan, Up flew the snowy ptarmigan. --Sir W.
                                                  Scott.

   5. (Mining) To extract, as ore or coal. --Raymond.

   Syn: To gain; get; procure; earn. See {Gain}.

Winning \Win"ning\, a.
   Attracting; adapted to gain favor; charming; as, a winning
   address. ``Each mild and winning note.'' --Keble.

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
     See {win}

winning
     adj 1: bringing success; "the winning run"
     2: having won; "the victorious entry"; "the winning team" [syn:
         {victorious}]
     3: very attractive; capturing interest; "a fetching new
        hairstyle"; "something inexpressibly taking in his
        manner"; "a winning personality" [syn: {fetching}, {taking}]
     n : succeeding with great difficulty; "winning is not
         everything"

win
     n 1: a victory (as in a race or other competition); "he was happy
          to get the win"
     2: something won (especially money) [syn: {winnings}, {profits}]
        [ant: {losings}]
     [also: {won}, {winning}]

win
     v 1: be the winner in a contest or competition; be victorious;
          "He won the Gold Medal in skating"; "Our home team won";
          "Win the game" [ant: {lose}]
     2: win something through one's efforts; "I acquired a passing
        knowledge of Chinese"; "Gain an understanding of
        international finance" [syn: {acquire}, {gain}] [ant: {lose}]
     3: obtain advantages, such as points, etc.; "The home team was
        gaining ground"; "After defeating the Knicks, the Blazers
        pulled ahead of the Lakers in the battle for the
        number-one playoff berth in the Western Conference" [syn:
        {gain}, {advance}, {pull ahead}, {make headway}, {get
        ahead}, {gain ground}] [ant: {fall back}]
     4: attain success or reach a desired goal; "The enterprise
        succeeded"; "We succeeded in getting tickets to the show";
        "she struggled to overcome her handicap and won" [syn: {succeed},
         {come through}, {bring home the bacon}, {deliver the
        goods}] [ant: {fail}]
     [also: {won}, {winning}]