IPA: /ˈwɪn.ləs/
KK: /ˈwɪn.ləs/
Not having achieved a victory or success in a competition or contest.
The team ended the season with a winless record, having lost all their games.
Winless → It is formed from "win" (from Old English "winnan", meaning to strive or gain victory) and "-less" (meaning without). The word "winless" describes a state of being without victories or wins.
Think of someone who has not achieved a victory — 'win' means to gain a victory, and '-less' means without.