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As a specialist in soul music, in the 1970s Wingfield contributed regular articles and reviews to the monthly journal Let It Rock, and the weekly Melody Maker among others. As a performer, he played with the British soul band The Olympic Runners, and Albert Lee & Hogan's Heroes.
In 1971, Wingfield played the piano on the B. B. King in London album, and in the following year received similar credits for Seventy-Second Brave, the Keef Hartley Band album. Wingfield played keyboards on Bryn Haworth's 1974 album, Let the Days Go By and on his 1975 follow-up Sunny Side of the Street. In 1983, Wingfield played keyboards on Haworth's album, Pass It On.
Wingfield hit the singles charts on both sides of the Atlantic in 1975 with "Eighteen With a Bullet", a pastiche doo-wop number involving word play on hit record chart positions. (A "bullet", in record-chart parlance, refers to a song still selling strongly and/or moving up the charts). On the Billboard Hot 100 for the week ending November 22, 1975, the tune lived up to its name by charting at no. 18 — with a bullet. The song peaked at no. 15 a week later. It also reached no. 7 in the UK Singles Chart. Taken from the album, Breakfast Special, "Eighteen With A Bullet" would later be featured on the soundtrack to the 1998 film, Lock, Stock and Two Smoking Barrels.
In 1977, his song "Making a Good Thing Better" appeared on Olivia Newton-John's album of the same name. Between 1975 and 1981, Wingfield played keyboards with The Hollies. In 1980, he produced the first album by Dexys Midnight Runners, Searching for the Young Soul Rebels. In the 1980s, Wingfield teamed up with the film producer Mel Brooks, and co-wrote the songs "It's Good To Be the King" and "To Be or Not to Be (The Hitler Rap)". In 1985, he produced the Kane Gang's debut album Bad and Lowdown World of the Kane Gang. Three years later his production credits appeared on The Proclaimers UK Top 20 hit, "I'm Gonna Be (500 Miles)", and their album Sunshine on Leith.
The Pasadenas 1988 song, "Tribute (Right On)", was written by Wingfield.
Wingfield played with Van Morrison at the 1974 Montreux Jazz Festival, which was one of the two shows featured on Morrison's first DVD (2006). Several years later, Wingfield also did a summer tour of Europe with Morrison's band, featuring the songs from the latter's 1979 album, Into the Music. Beginning with their 1983 reunion shows, Wingfield spent eighteen years handling keyboard duties for The Everly Brothers.