Old English winn "labor, toil; strife, conflict; profit, gain," from the source of win (v.). Modern sense of "a victory in a game or contest" is first attested 1862, from the verb.
-less
word-forming element meaning "lacking, cannot be, does not," from Old English -leas, from leas "free (from), devoid (of), false, feigned," from Proto-Germanic *lausaz (cognates: Dutch -loos, German -los "-less," Old Norse lauss "loose, free, vacant, dissolute," Middle Dutch los, German los "loose, free," Gothic laus "empty, vain"), from PIE root *leu- "to loosen, divide, cut apart." Related to loose and lease.