The band had previously released Brothers and Sisters in 1973 to critical and commercial success. The group toured the following year, attracting large crowds and earning substantial amounts of money, all while internal tension grew among the members. Vocalist and keyboardist Gregg Allman and vocalist and guitarist Dickey Betts released solo albums — The Gregg Allman Tour and Highway Call, both issued that fall — which prompted speculation on the band's unity.
When the band regrouped to work on Win, Lose or Draw, unresolved issues arose in rehearsals. The band was particularly critical of Allman's decision to move to Los Angeles, as well as his tabloid relationship with pop star Cher. With miscommunication and anger at an all-time high, the band pieced together the album over a period of several months, in stark contrast to their usual recording methods. Band members often could not be present in the studio at the same time.
Reviews of the album were negative, commenting on a lack of energy, formulaic songwriting, and indifferent sound. The album reached number 5 on the Billboard 200 albums chart based on their previous popularity. The record had been highly anticipated a year earlier, but now the Allmans' moment was passing.
The group's first two studio releases, The Allman Brothers Band (1969) and Idlewild South (1970) (both released by Capricorn Records), stalled commercially, but their 1971 live release, At Fillmore East, represented an artistic and commercial breakthrough. The album features extended renderings of their songs "In Memory of Elizabeth Reed" and "Whipping Post", and is considered among the best live albums ever made.