winningest

From winning +‎ -est.

• IPA^(key): /ˈwɪnɪŋɪst/

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, 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