Pyle joined Phil Miller, a friend from kindergarten, and Phil's brother Steve, in forming Bruno's Blues Band, which rapidly evolved into Delivery. However, Pyle left the band in 1970 after arguing with singer Carol Grimes. He briefly played in blues band Chicken Shack and Steve Hillage's band Khan.[3]
In 1984, Pyle met Sophia Domancich and the two had a relationship until 1990. Pyle also started his own band, Pip Pyle's Equip'Out, including Domancich. Equip'Out released Equip'Out, Up! and Instants. He released one solo album, Seven Year Itch, in 1998 with guests including Miller, Sinclair, Stewart, Dean (saxello), Hopper (bass), Jakko Jakszyk, Barbara Gaskin, John Greaves (vocals), François Ovide, Fred T. Baker (bass), Paul Rogers (double bass), Lydia Domancich (piano, Sophia's sister) and Didier Malherbe (alto sax). Pyle also played in Miller's band In Cahoots from 1982 to 2001, appearing on Cutting Both Ways, Split Seconds, Live 86-89, Live in Japan, Recent Discoveries, Parallel and Out of the Blue.
His last projects were his group Bash!, featuring the French guitarist Patrice Meyer, Fred Baker on bass and Alex Maguire on keyboards, and a Hatfield and the North reunion (also with Maguire). Bash! released the live album Belle Illusion (Cuneiform Records), but only played five live shows in total (including Progman Cometh), finding it difficult to attract interest from venues.
In 2005 Pyle joined Phil Miller and Richard Sinclair in a re-formation of Hatfield and the North, with Alex Maguire handling the keyboards. On 29 January, all three were reunited for the first time in fifteen years when Pyle sat in with the Richard Sinclair Band for a few old numbers ("Above And Below", "Share It", "Halfway Between Heaven And Earth" and "Didn't Matter Anyway") during a gig at Whitstable's Horsebridge Arts Centre. The rejuvenated Hatfield made its official live debut on 18 March 2005 at the Mean Fiddler in London, and a brief tour of Europe followed in June. More international touring followed in 2005–06, including dates in Japan, Mexico, the US and Europe. On 26 August 2006 Pyle played his last gig in Feerwerd (Groningen), Netherlands.