Entry 4 senses · 2 variants Webster, 1913 Winning /wĭn'-ĭng/ · Win·ning · IPA /ˈwɪnɪŋ/ a. n. 01 a. Attracting; adapted to gain favor; charming; as, a winning address. 1. Attracting; adapted to gain favor; charming; as, a winning address. 02 n. The act of obtaining something, as in a contest or by competition. 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. A new opening.(Mining) Phrases & compounds Winning headway — an excavation for exploration, in post-and-stall working. Winning post — the post, or goal, at the end of a race.