Origin and history of no-win

"not in any degree, not at all," Middle English, from Old English na, from ne "not, no" + a "ever." The first element is from Proto-Germanic *ne (source also of Old Norse, Old Frisian, Old High German ne, Gothic ni "not"), from PIE root *ne- "not." Second element is from Proto-Germanic *aiwi-, extended form of PIE root *aiw- "vital force, life, long life, eternity." Ultimately identical to nay, and the differences of use are accidental.

As an adjective, "not any, not one, none" (c. 1200) it is reduced from Old English nan (see none), the final -n omitted first before consonants and then altogether. As an interjection making a negative reply to a statement or question, "not so," early 13c., from the adverb. As a noun, 1580s as "a denial; a negative vote," 1650s as "person who casts a negative vote."

Construction no X, no Y is attested from 1530s (in no peny no pardon). No problem as an interjection of assurance is attested by 1963. No way as a colloquial expression meaning "it can't be done" is attested by 1968 (noway (adv.) "not at all, in no respect, by no means" is from c. 1300). No-knock (adj.) in reference to police raids without permission or warning is by 1970, American English. Phrase no can do "it is not possible" is attested from 1827, a locution of English-speaking Chinese noted 19c. in China, Australia, and the West Coast of the United States.

We repeated our advice again and again, but got no answer but a loud horse-laugh, and their national maxim of No can do: Europe fashion no do in China. ["Reminiscences of a Voyage to and from China," in Paxton's Horticultural Register, London, 1836]

"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."