In the late 1970s and early 1980s, Winslow recorded for Warner Bros. Records. Briefly married to her record producer, Ray Ruff, in 1979 she had her biggest hit single with, "Say You Love Me," which reached No. 10 on the Billboard country chart. In 1980 her cover version of Roy Orbison's "Crying," became Winslow's second major hit single, peaking at No. 14. She had a series of minor hits on the Billboard country chart under Warner Bros., and eventually signed with MCA Records, releasing her final single with the label in 1984, a cover of "Baby, Come to Me."