In the early 2000s Gaughan turned his hand to larger-scale composition and received two orchestral commissions from the Celtic Connections festival. The first, "Timewaves (Love Song to a People's Music)", mixed orchestral playing with folk singing and was performed at the 2004 festival by the Orchestra of Scottish Opera together with Gaughan and other folk singers and players. The second was a symphony, "Treaty 300", composed for the inaugural concert of the Celtic Connections Youth Orchestra in 2007. Between 2001 and 2008 five Gaughan albums were released. On "Outlaws and Dreamers" (2001), he used only his acoustic guitar and Brian McNeill's fiddle to accompany his voice. "Prentice Piece" (2002) was a self-selected thirty-year retrospective of his career (although some material could not be included owing to copyright disputes). "The Definitive Collection" (2006) was another compilation. "Lucky For Some" (2006) consisted almost entirely of self-written songs and "Gaughan Live! at the Trades Club" (2008) was a live gig, recorded at one of his favourite venues, the Trades Club, Hebden Bridge, Yorkshire.