Antonyms of adj winless

1 sense of winless

Sense 1
winless -- (having no wins; "the team had a very disappointing winless season")

INDIRECT (VIA unsuccessful) -> successful -- (having succeeded or being marked by a favorable outcome; "a successful architect"; "a successful business venture")

Similarity of adj winless

1 sense of winless

Sense 1
winless -- (having no wins; "the team had a very disappointing winless season")
       => unsuccessful (vs. successful) -- (not successful; having failed or having an unfavorable outcome)