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Crossword clues for winless

Douglas Harper's Etymology Dictionary
winless

1948, from win (n.) + -less.

Wiktionary
winless

a. 1 Having never won 2 Without a win; unsuccessful

WordNet
winless

adj. having no wins; "the team had a very disappointing winless season"

Usage examples of "winless".

What an upset, if the winless boxer brought down the invincible karateka!

Lache was too proud to be drawn into a winless fight like some rutting elk, and certainly not under the Jarman roof!