Having started his musical career 1966-67 with the Wilde Flowers, he founded Caravan in 1968 with his cousin Richard Sinclair (bass/vocals), Pye Hastings (guitar/vocals), and Richard Coughlan (drums) and was in and out of the band for 35 years (so far 1968-71, 1973–75, 1979–82, 1990–2002). Over the course of Caravan's first three albums he developed his playing enormously on his favoured model of Hammond organ, the A100, culminating in his soaring work on what is perhaps their famous album, In the Land of Grey and Pink (1971). "Calyx, The Canterbury Website" refers to him as "master of the typical Canterbury organ sound/playing". However, from the second album onwards, he also added other keyboards to his palette, including piano, harpsichord and Mellotron. On his return to Caravan for their fifth album, For Girls Who Grow Plump in the Night, he pioneered the Davolisint.
In the early 2000s he released two solo albums, Full Circle and Into the Sun (both 2003). Since then, he has been engaged in a solo career, including concert appearances in Japan and England. A 30th anniversary re-release of his Moon Over Man album featuring vocalist Tim Lynk (demos for an unreleased solo album recorded 1976-77, originally issued on CD by Voiceprint in 1993) appeared in 2006 (including improved sound and bonus tracks), although this is due to be superseded by a further enhanced release of the same material some time in the near future. Two solo albums, PianoWorks1 - Frozen In Time and Stream (the latter featuring several distinguished guest artists) were released in 2010 and 2011 respectively, but licensing problems have so far prevented Stream from being officially issued outside Japan. However, Dave Sinclair's most recent solo album, The Little Things, was released in 2013, the Japanese version being slightly different in packaging and content from the international version. Major concert dates with saxophonist Jimmy Hastings are scheduled in Japan for May 2015.