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From winning +‎ -est.




  1. superlative form of winning: most winning
    1. (US) Most winning; most attractive.
      She has the winningest smile.
  2. 3 (US, sports) Having the most wins.
      • 1958, Charles Beaumont and William F. Nolan (editors), Omnibus of Speed: An Introduction to the World of Motor Sport,[1] Putnam, page 183,
        There can be little doubt that Carroll Shelby deserves the high praise he has received from many quarters. On the record he’s America’s winningest big car driver.
      • 1996, David F. Salter, Crashing the Old Boys’ Network: The Tragedies and Triumphs of Girls and Women in Sports,[2] Greenwood Publishing Group, →ISBN, page 83,
        [Jody Conradt] is the winningest all-time coach in women's basketball with more than 650 victories.
      • 2004, Walter Harvey, The Super Bowl’s Most Wanted: The Top 10 Book of Big-Game Heroes, Pigskin Zeroes, and Championship Oddities,[3] Brassey’s, →ISBN, page 42,
        In just a few short years, Don Shula turned the Dolphins from a laughingstock expansion team into an NFL dynasty. He then went on to become the winningest coach in NFL history.