Winwood's self-titled debut album was released on Island Records in June 1977. Although the album peaked at No. 12 in the United Kingdom and in the Top 40 in the United States, its singles failed to gain success in either country. His second album Arc of a Diver was issued in December 1980, and was certified Platinum in the United States and Silver in the United Kingdom. Its first track, "While You See a Chance", became a major hit in the United States, reaching No. 7 on the Billboard Hot 100. His 1982 follow-up album Talking Back to the Night did not produce any hits in the United States. However, its lead single "Still in the Game" reached No. 19 on the Canadian Singles Chart, and the second single, "Valerie", charted at No. 13 on the Mainstream Rock Tracks chart.
Back in the High Life (1986) was aimed more towards pop music, selling three million copies in the United States. The single "Higher Love" (taken from the album) became Winwood's first number one hit on the Billboard Hot 100 and Canadian Singles Chart, while also peaking at No. 13 on the UK Singles Chart. "Freedom Overspill", "Back in the High Life Again" and "The Finer Things" became major hits in the United States between 1986 and 1987. His fifth album Roll with It was released on Virgin Records in 1988, with the title track released as the lead single. That song became Winwood's second number one single on the Canadian Singles Chart and the Billboard Hot 100. However, it only became a minor hit in the United Kingdom, reaching No. 53. "Don't You Know What the Night Can Do?" and "Holding On" both became major hits on the Hot 100 and Hot Adult Contemporary Tracks chart in 1988. Refugees of the Heart (1990) contained more soul-inspired elements, debuting at No. 26 on the UK Albums Chart and No. 27 on the Billboard 200. Although its first single "One and Only Man" was only a minor UK hit, it reached No. 5 in Canada and No. 18 in the United States.
Top 100 (Kent Music Report) peaks to 12 June 1988: Kent, David (1993). Australian Chart Book 1970–1992 (Illustrated ed.). St Ives, N.S.W.: Australian Chart Book. p. 342. ISBN0-646-11917-6.
Top 50 (ARIA) peaks from 13 June 1988: "Discography Steve Winwood". australian-charts.com. Hung Medien. Retrieved 18 February 2014.
Top 100 (ARIA) peaks from January 1990 to December 2010: Ryan, Gavin (2011). Australia's Music Charts 1988–2010 (PDF ed.). Mt. Martha, VIC, Australia: Moonlight Publishing. p. 305.
"One and Only Man": "RPM 100 Hit Tracks"(PDF). RPM. Vol. 53, no. 19. 19 January 1991. p. 6. Retrieved 20 August 2022. See previous week's position for peak as that chart was not published.