He has toured in bands, provided backup for well-known musicians, and written songs that have been covered by Kim Carnes, Norma Waterson and Nanci Griffith.

Gregson cites a wide range of musical influences and tastes and has stated that his all-time favourite record is Nick Drake's Pink Moon.

Having recorded and released Gregson's composition Yesterday's Love as an indie single in 1979 Any Trouble began to receive airplay courtesy of BBC Radio 1 DJs John Peel, Andy Peebles and others in the UK.

In 1984, shortly after the release of Any Trouble's fifth album Wrong End of the Race, Gregson saw vocalist Christine Collister perform at Poynton Folk Club, Cheshire, England.

[3] The Gregson and Collister musical partnership proved popular and productive, producing five albums and earning them the attribution "the state of the art in British folk-rock" by Rolling Stone.

In addition to Richard Thompson, he has collaborated with many other artists, including Nanci Griffith (1996–2007), Eddi Reader and Boo Hewerdine, founder member of The Bible (1993 & 1999) and Plainsong (1997).

Gregson's reputation as a songwriter has led to his songs being recorded by artists, including Nanci Griffith (I Love This Town), Kim Carnes (Touch and Go), Fairport Convention (Home Is Where the Heart Is), Claire Martin (Could This Be the One?

[10][11] In 2011, Gregson joined forces with guitarist Mark Griffiths and Andy Roberts to form 3 Boxes, an instrumental guitar trio, to play a series of gigs and record an album of original material.

In 2013, 3 Boxes released their only album to date Strings Attached, including only material written by the three members, all instrumentals for three acoustic guitars recorded live in the studio by producer John Wood.