winningest

From winning +‎ -est.

• IPA^(key): /ˈwɪnɪŋɨst/

winningest

1. superlative form of winning: most winning
   1. (US) Most winning; most attractive.

      She has the winningest smile.

2. (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, 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, 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, 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.

• losingest

• entwinings