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Definition of winning : 1. A new opening.
2. Attracting; adapted to gain favor; charming; as, a winning address.
3. The act of obtaining something, as in a contest or by competition.
4. The money, etc., gained by success in competition or contest, esp, in gambling; - usually in the plural.
5. The portion of a coal field out for working.

Synonyms:

gentle, benignant, adrift, fascinating, lovely, cute, beguiling, bewitching, undone, sweet, prepossessing, leading, pretty, endearing, amiable, dear, captivating, behind, lovesome, pleasant, prize-winning, kind, precious, pleasing, tempting, delightful, gratifying, eye-catching, ugly, winningest, repulsive, darling, successful, nip and tuck, enchanting, nice-looking, loving, stunning, harming, glamorous, insinuating, triumphal, acceptable, engaging, courteous, appealing, adorable, award-winning, lovable, champion, winsome, attractive, triumphant, disarming, blue-ribbon, victorious, charming, like, good-natured, enticing, agreeable, rival

achieving, seizing, catching, snaring, taking, abducting, apprehending, obtaining, securing, snatching, getting, collaring, occupying, arresting, capturing, gaining

mastering, beating, outplaying, subduing, routing, quelling, crushing, predominating, subjecting, conquering, checkmating, outdoing, trumping, humbling, vanquishing, overthrowing, trouncing, whipping, defeating, foiling, overpowering, overturning

collecting, palming, heaping, accumulating, buying, landing, annexing, garnering, claiming, incurring, procuring, fetching, reaping, pocketing, adding, luring, cornering, netting, acquiring, scoring, retrieving, purchasing, wrangling, harvesting, assuming, amassing, bagging, receiving

lording, bettering, presiding, oppressing, overseeing, ruling, commanding, controlling, subordinating

conquest, ascendancy, knockout, K.O., subdual, mastery, victory, subjection, checkmate, grand slam, success, win, achievement, kill, triumph

dominating, surmounting, accomplishing, earning, fulfilling, attaining, triumphing, consummating, succeeding, overcoming, prevailing, ascending

Usage examples:

• Because be knew that he, not she, was winning, he picked her up in his arms and kissed her as if she were a child. - "King--of the Khyber Rifles", Talbot Mundy.
• Do you think we've got any chance of winning? - "Down the Slope", James Otis.
• I had much more in view just then than the mere winning of the game. - "By Wit of Woman", Arthur W. Marchmont.