Hank Williams recorded "You Win Again" on July 11, 1952 - one day after his divorce from Audrey Williams was finalized. Like "Cold, Cold Heart," the song was no doubt inspired by his tumultuous relationship with his ex-wife, as biographer Colin Escott observes:
"It might have been no more than coincidence, but, in the absence of hard evidence to the contrary, the songs cut that day after Hank's divorce seem like pages torn from his diary...Its theme of betrayal had grown old years before Hank tackled it, but, drawing from his bottomless well of resentment, he gave it a freshness bordering on topicality." 
In Williams' original draft, the song had been titled "I Lose Again" but was reversed at producer Fred Rose's insistence. The song's memorable opening line, "The news is out all over town," begins the story of an utterly defeated narrator who cannot bring himself to leave his love despite her infidelities. It was recorded at Castle Studio in Nashville with Jerry Rivers (fiddle), Don Helms (steel guitar), and Harold Bradley (rhythm guitar), while it is speculated that Chet Atkins played lead guitar and Ernie Newton played bass.
"You Win Again" was released as the B-side to "Settin' the Woods on Fire," primarily because up-tempo, danceable numbers were preferable as A-sides for radio play and for the valuable jukebox trade. Nonetheless, "You Win Again" peaked at number ten on the Most Played in C&W Juke Boxes chart, where it remained for a single week.