"be successful or victorious" in a game, contest, or battle, c. 1300, winnen, a fusion of Old English winnan "to labor, toil, struggle for, work at; contend, fight," and gewinnan "to gain or succeed by struggling, conquer, obtain." Both are from Proto-Germanic *wennanan "to seek to gain," which is reconstructed to be from PIE root *wen- (1) "to desire, strive for," which Boutkan calls "a clearly reconstructable root with different semantic developments," but probably originally "want," hence "try to obtain."
The sense of "exert effort" in early Middle English faded into "earn (things of value) through effort" (c. 1300) but lingers in breadwinner. For sense evolution from "work for" to "obtain," compare get, gain.
Related: Won; winning. The meaning "gain the affection or esteem of" (win friends) is by late 14c., in Middle English you also could win enemies.
Phrase you can't win them all is attested by 1886 in sports-writing, a verbal shrug in reaction to a loss.
The Detroit Baseball Club may win two games out of three with Chicago, but it can't win them all, for Chicago took one to-day. [New York Times, July 9, 1886]
Germanic cognates include 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."
