The Collaborative International Dictionary of English v.0.48:

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.]
   [1913 Webster]
   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.
      [1913 Webster]

            Thy well-breathed horse
            Impels the flying car, and wins the course.
                                                  --Dryden.
      [1913 Webster]

   2. To allure to kindness; to bring to compliance; to gain or
      obtain, as by solicitation or courtship.
      [1913 Webster]

            Thy virtue wan me; with virtue preserve me. --Sir P.
                                                  Sidney.
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            She is a woman; therefore to be won.  --Shak.
      [1913 Webster]

   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.
      [1913 Webster]

   4. To come to by toil or effort; to reach; to overtake.
      [Archaic]
      [1913 Webster]

            Even in the porch he him did win.     --Spenser.
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            And when the stony path began,
            By which the naked peak they wan,
            Up flew the snowy ptarmigan.          --Sir W.
                                                  Scott.
      [1913 Webster]

   5. (Mining) To extract, as ore or coal. --Raymond.
      [1913 Webster]

   Syn: To gain; get; procure; earn. See Gain.
        [1913 Webster]

The Collaborative International Dictionary of English v.0.48:

Winning \Win"ning\, a.
   Attracting; adapted to gain favor; charming; as, a winning
   address. "Each mild and winning note." --Keble.
   [1913 Webster]

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

Moby Thesaurus II by Grady Ward, 1.0:

167 Moby Thesaurus words for "winning":
   Cadmean victory, KO, Pyrrhic victory, acceptable, accession,
   acquirement, acquisition, addition, admirable, adorable, agreeable,
   alluring, angelic, appealing, appetizing, ascendancy, ascendant,
   attainment, attractive, authoritative, beguiling, bewitching,
   blandishing, cajoling, captivating, caressable, catching,
   championship, charismatic, charming, coaxing, come-hither,
   coming by, conquering, conquest, consequential, coquettish,
   cuddlesome, defeating, delightful, desirable, dominant,
   dragging down, dulcet, earnings, easy victory, effective,
   effectual, efficacious, enchanting, engaging, enravishing,
   enthralling, enticing, entrancing, enviable, estimable, exciting,
   exotic, exquisite, fascinating, fetching, flirtatious,
   flushed with success, gaining, getting, getting hold of, glamorous,
   grand slam, heart-robbing, hypnotic, important, in ascendancy,
   in the ascendant, influential, interesting, intriguing, inviting,
   irresistible, kissable, knockout, landslide, landslide victory,
   likable, lovable, lovely, lovesome, luxurious, magnetic, making,
   mastery, mesmeric, momentous, moneygetting, moneygrubbing,
   moneymaking, moral victory, mouth-watering, obtainment, obtention,
   overcoming, personable, persuasive, picnic, piquant, pleasing,
   potent, powerful, prepossessing, prestigious, prevailing, procural,
   procurance, procuration, procurement, provocative, provoquant,
   pushover, ravishing, reputable, runaway victory, securement,
   seducing, seductive, sensuous, seraphic, siren, sirenic,
   spellbinding, spellful, strong, suasive, subdual, subduing,
   substantial, success, successful, sweet, taking, tantalizing,
   teasing, telling, tempting, thrilling, tickling, titillating,
   titillative, to be desired, toothsome, total victory, triumph,
   triumphal, triumphant, trover, unobjectionable, vanquishing,
   victorious, victory, voluptuous, walkaway, walkover, weighty, win,
   winning streak, winsome, witching, worth having