winningest

adj

1. (form-of, superlative)superlative form of winning: most winning
2. (US)superlative form of winning: most winning

   “She has the winningest smile.”

3. (US)Having the most wins.

   “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.”

   “[Jody Conradt] is the winningest all-time coach in women's basketball with more than 650 victories.”

   “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.”

   “[Johannes Klæbo winning six gold medals at the 2026 Winter Olympics] also extends Mr. Klæbo’s record as the winningest Winter Olympian in history with his 11th gold medal, second only to American swimmer Michael Phelps’ 23 in the entire Olympic movement.”