Dunkley's recording career began in 1965, when he was fourteen, with "Gypsy" (a duet with Roy Shirley) for Linden Pottinger's Gaydisc label, "My Queen" (with Junior English) for Prince Buster, and "Love Me Forever" on the Rio label. Between 1967 and 1968 he recorded several singles for Joe Gibbs including "Please Stop Your Lying" (1967) and "Love Brother" (1968), before switching to Coxsone Dodd in 1969.
In the early 1970s, together with Gregory Isaacs he formed the African Museum record label, although Isaacs soon took sole control of the label, while Dunkley formed a new label, Silver Ring. In 1972 he teamed up with producer Jimmy Radway for two of his most popular singles, "Keep The Pressure On" and "Black Cinderella". The same year saw the release of Dunkley's Sonia Pottinger produced debut album, Presenting Errol Dunkley, which included the track "A Little Way Different".
Dunkley continued to record throughout the 1970s and towards the end of the decade his popularity in the UK grew, resulting in a breakthrough UK Singles Chart hit in 1979 with "OK Fred", a cover version of a John Holt-penned song, that reached number 11. His 1980 release "Sit Down And Cry" also reached the charts.
Dunkley re-recorded his biggest hit, "OK Fred", in 1996 with Queen Sister *N*.