 On 24 June 2008, Duguid ended his 14-year association with Colchester by signing a two-year contract with Championship club Plymouth Argyle, for an undisclosed fee.Duguid made his Argyle debut on 9 August 2008, starting the club's first league game of the 2008–09 season, against Wolverhampton Wanderers in a 2–2 draw.He soon became a fan favourite, and his first goal for the Pilgrims was a crucial one – it came at Watford in a 2–1 win, giving Argyle their first win of the season.