After leaving his coaching role at Colchester in October 2014, Duguid returned to playing with Stanway Rovers the same month, before joining Welling United in the Conference in January 2015.
He returned to Stanway after two months with Welling, before making a move to Needham Market in the summer of 2015, where he became academy manager alongside former Colchester teammate Kemal Izzet.
[3] He missed a crucial penalty as Colchester lost the 1997 Football League Trophy Final in a shootout against Carlisle United.
Duguid's status with the Colchester fans was demonstrated when he was voted the club's best ever player in a poll to mark the centenary of the Professional Footballers' Association.
[4] 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.
[4] 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.
[5][6] Having spent time back with Colchester United for pre-season training,[7] Duguid signed a one-year contract with the club on 20 July 2011.
[11] In December 2012, Duguid was appointed player-coach, helping manager Joe Dunne establish a link between the first-team squad and the youth-team and their development.
[13][14][15] Duguid called time on his playing career in the 2013–14 season, and ended it by coming on as a substitute for Dominic Vose in a 1–0 win against Walsall on 3 May 2014.
[19] He made his debut for the club in an extra time victory over Hertford Town in the FA Vase, playing the full 120-minutes.
[24] Duguid made eleven appearances for the club before being named as head coach of Needham's north site academy on 8 October 2015 alongside former Colchester teammate Kemal Izzet who was head coach of the south site academy, taking over the role from former Northern Ireland international Kevin Horlock.