Cuthbert began his career in the youth system at Celtic and signed his first professional contract with the club in August 2003.
[5] Cuthbert joined Scottish First Division club Livingston on a one-month loan in order to gain first-team experience during the 2006–07 season, making four appearances.
[11] After leaving St Mirren, Cuthbert said a second loan spell was a possibility should he fail to secure a first-team place at Celtic.
[14] He was subsequently left out of the starting lineup for four matches until Swindon faced Wolverhampton Wanderers in the League Cup second round, which they lost 6–5 on penalties following a 0–0 draw after extra time.
[16][17] Towards the end of the season, Swindon were well-placed for promotion to the Championship, but with only one win in their last six matches, the club finished in fifth place and would have to contest the play-offs.
[28][29] Ahead of the 2011–12 season, on 3 June 2011, Cuthbert signed a two-year contract with League One club Leyton Orient.
[30] He made his Leyton Orient debut on the opening day of the campaign, playing as a centre back in a 1–0 defeat to Walsall.
[31] Cuthbert received a red card in a 3–1 defeat at home to AFC Bournemouth on 13 September 2011 and was subsequently suspended for three matches.
[34] Cuthbert suffered a hamstring injury on 31 March 2012, in a 2–0 defeat to Charlton Athletic, causing him to miss the final seven matches of the season.
[41] In a 0–0 draw with Preston North End on 23 March 2013, Cuthbert suffered a fractured metatarsal that caused him to miss the rest of the season.
[43] Cuthbert played most of the 2013–14 season at right back, as Leyton Orient came close to promotion to the Championship, ultimately losing on penalties to Rotherham United in the play-off final.
[57] On the opening day of the season, Cuthbert was initially named on the bench, but an injury to Alan Sheehan moments before kick-off meant he was called up to the starting lineup.
[61] After making 50 starting appearances in league matches for Luton, Cuthbert triggered a one-year contract extension to keep him at the club until June 2018.
[64] His run in the first-team was curtailed due to a groin injury sustained in Luton's 7–0 home win against Cambridge United on 18 November 2017.
[63][67] Cuthbert made 25 appearances in all competitions during the campaign, scoring twice, as Luton won promotion to League One after finishing in second place.
[71] Cuthbert made his Stevenage debut in the club's opening match of the 2018–19 season, a 2–2 draw with Tranmere Rovers at Broadhall Way.