After attending Bedford School, he studied at the Berklee College of Music in Boston, Massachusetts in 1978, before joining his parents' quintet.

Between 1980 and 1983 he toured the United States, Australia, and Europe with them, going on to work with Tommy Chase, the BBC Big Band, and Clark Tracey, with whom he recorded two albums.

Dankworth recorded an arrangement of Duke Ellington's Black, Brown, and Beige with violinist Nigel Kennedy in 1986, with whom he also performed Antonio Vivaldi's The Four Seasons.

He also played in the 1980s with Dick Morrissey, Spike Robinson, Jean Toussaint, Michael Garrick, Tommy Smith, Julian Joseph, and Andy Hamilton, as well as leading his own quartet.

He has played with Mose Allison, Clark Terry, Mel Tormé, Anita O'Day, Peter King, Alan Barnes, David-Jean Baptiste, Van Morrison and Martin Taylor, among others.