win·ning / ˈwining/ • adj. 1. gaining, resulting in, or relating to victory in a contest or competition: a winning streak. 2. attractive; endearing: a winning smile. • n. 1. (winnings) money won, esp. by gambling: he went to collect his winnings. 2. Mining a shaft or pit together with the apparatus for extracting coal or other minerals. DERIVATIVES: win·ning·ly adv. (in sense 2 of the adjective ).