Synonyms of winningest

Adjective

1. victorious, winning, successful (vs. unsuccessful)

usage: having won; "the victorious entry"; "the winning team"

2. fetching, taking, winning, attractive (vs. unattractive)

usage: very attractive; capturing interest; "a fetching new hairstyle"; "something inexpressibly taking in his manner"; "a winning personality"

Definition and meaning of winningest (Dictionary)