Celtic Born in
Alexandria, West Dunbartonshire, He went on to
captain the club's under-19 and reserve teams.
Loan spells 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. He was loaned out once again, this time on a season-long loan to
Scottish Premier League club
St Mirren in August 2008. He made his debut in a 0–0 draw with
Kilmarnock on 16 August. Cuthbert made 34 appearances in all competitions before returning to Celtic.
Swindon Town Despite interest from former loan club St Mirren, Cuthbert signed for
League One club
Swindon Town on 13 July 2009, on a two-year contract for a fee thought to be £100,000. Cuthbert made his debut for Swindon on the opening day of the
2009–10 season in a 5–0 defeat away to
Gillingham. 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. Cuthbert scored his first goal for Swindon four days later in a 2–1 win at home to
Southend United. 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. Swindon defeated Charlton 5–4 on penalties after their two-legged semi-final ended 3–3 after extra time. Cuthbert later said the success of getting to
Wembley Stadium in his first season with the club was a dream come true. The
play-off final saw Swindon lose 1–0 to
Millwall, preventing the club from gaining promotion to the Championship. At the start of the
2010–11 season, Cuthbert was named as the club's vice-captain. He scored his first goal of the season in a 2–1 defeat away to
Milton Keynes Dons on 28 August 2010. Six months later, Cuthbert scored his second goal of the season in a 2–1 defeat away to
Colchester United on 12 February 2011. In March, Cuthbert suffered a fractured cheekbone in a 1–1 draw with
Dagenham & Redbridge, but was told he did not need surgery. Swindon were relegated to
League Two after a 3–1 defeat away to
Sheffield Wednesday on 25 April. Following the completion of the season, Cuthbert reflected on a mistake he made during a 2–1 defeat at home to
Notts County, two days before Swindon were relegated, and was intent on returning the following season as a better player. However, Cuthbert was not offered a new contract, despite expressing a desire to remain with the club.
Leyton Orient Ahead of the
2011–12 season, on 3 June 2011, Cuthbert signed a two-year contract with League One club
Leyton Orient. 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. 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. Cuthbert scored his first goal for the club on 8 October in a 3–2 win over
Scunthorpe United. At the end of October, Cuthbert was nominated for the
League One Player of the Month award. 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. Despite his injury, Cuthbert was named Leyton Orient's Player of the Year for the 2011–12 season. Shortly after receiving it, Cuthbert said that winning the award was a proud moment for him. Cuthbert made a recovery from his injury ahead of a
friendly match with
Ebbsfleet United in pre-season ahead of the
2012–13 campaign. After just two appearances, Cuthbert again suffered a hamstring injury that kept him from playing until December 2012. In the
Football League Trophy southern section semi-final at home to
Yeovil Town, Cuthbert provided a winning
assist for
Dave Mooney in a 1–0 win to send the club through the southern section final. 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. Shortly after the end of the season, Cuthbert signed a new two-year contract with the club. 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. Cuthbert played in 54 matches in all competitions over the season, scoring four goals. After the season ended, Cuthbert was not offered a new contract. Following his departure, Cuthbert stated that the club told him to wait by the phone to find out if he would be offered a new contract upon the expiry of his deal, which he "wasn't set on waiting about to be told whether I was wanted or not".
Luton Town Cuthbert signed a two-year contract with League Two club
Luton Town on 26 May 2015. Upon his arrival, Cuthbert stated "The aim is promotion – I wouldn't have come to this club if I didn't think that was possible." Cuthbert was
sent off in second half
stoppage time for a
professional foul during a 3–2 defeat away to Notts County on 12 September. After the departure of
Steve McNulty who joined
National League club
Tranmere Rovers on loan in October, Cuthbert was named temporary club captain, but was only given the role on a permanent basis after
Nathan Jones replaced
John Still as manager in January 2016. Cuthbert went off injured during a 1–0 defeat at home to
Stevenage on 2 April, but despite his return to training prior to the penultimate match of the season against
Northampton Town on 30 April, he did not add to his tally of 40 appearances during the season. 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. Luton went on to achieve a 3–0 win away to
Plymouth Argyle, after which Cuthbert was praised for his performance by Jones. His performance also earned him a place in the
English Football League Team of the Week. 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. The
2017–18 season began with Cuthbert once again a first-team regular in the centre of defence for Luton. 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. The injury was initially expected to keep him out of action until January 2018, Cuthbert made 25 appearances in all competitions during the campaign, scoring twice, as Luton won promotion to League One after finishing in second place. He was released by Luton at the end of the season.
Stevenage Following his departure from Luton, Cuthbert signed for League Two club Stevenage on 30 May 2018. He joined the Hertfordshire club on a two-year contract. 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. Cuthbert was named as Stevenage's Player of the Year at the club's end-of-season awards ceremony on 4 May 2019.
Woking On 17 June 2022, Cuthbert agreed to join
National League club
Woking on a one-year deal. On 21 February 2023 Cuthbert scored his first goal for Woking a header from a corner in a 2-1 Win against Bromley. ==Coaching career==