Win
Old English winnan ‘strive, contend’ also ‘subdue and take possession of, acquire’, of Germanic origin.
wiktionary
From Middle English winnen, from Old English winnan(“to labour, swink, toil, trouble oneself; resist, oppose, contradict; fight, strive, struggle, rage; endure”) (compare Old English ġewinnan(“conquer, obtain, gain; endure, bear, suffer; be ill”)), from Proto-Germanic *winnaną(“to swink, labour, win, gain, fight”), from Proto-Indo-European *wenh₁-(“to strive, wish, desire, love”). Cognate with Low German winnen, Dutch winnen, German gewinnen, Norwegian Bokmål vinne, Norwegian Nynorsk and Swedish vinna.
From Middle English winn, winne, from Old English winn(“toil, labor, trouble, hardship; profit, gain; conflict, strife, war”), from Proto-Germanic *winną(“labour, struggle, fight”), from Proto-Indo-European *wenh₁-(“to strive, desire, wish, love”). Cognate with German Gewinn(“profit, gain”), Dutch gewin(“profit, gain”).
From Middle English wynne, winne, wunne, from Old English wynn(“joy, rapture, pleasure, delight, gladness”), from Proto-West Germanic *wunnju, from Proto-Germanic *wunjō(“joy, delight, pleasure, lust”), from Proto-Indo-European *wenh₁-(“to strive, wish, desire, love”).
Cognate with German Wonne(“bliss, joy, delight”), archaic Dutch wonne(“joy”), Danish ynde(“grace”), Icelandic yndi(“delight”).
From wind.
etymonline
win (v.)
"be victorious," c. 1300 fusion of Old English winnan "to labor, toil, struggle for, work at, strive, fight," and gewinnan "to gain or succeed by struggling, conquer, obtain," both from Proto-Germanic *wennanan "to seek to gain" (source also of Old Saxon winnan, Old Norse vinna, Old Frisian winna, Dutch winnen "to gain, win," Danish vinde "to win," Old High German winnan "to strive, struggle, fight," German gewinnen "to gain, win," Gothic gawinnen "to suffer, toil"), from PIE root *wen- (1) "to desire, strive for."
Related: Won; winning. Meaning "gain the affection or esteem of" is from c. 1600. Breadwinner preserves the sense of "toil" in Old English winnan. Phrase you can't win them all (1954) first attested in Raymond Chandler. Winningest is attested by 1804.
win (n.)
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.
