Born in Perth, Cuthbert made his St Johnstone debut in September 2001 after an injury to Alan Main. He remained in goal for the following two games, after which Main returned only to break his leg. Instead of turning to Cuthbert again, then-manager Sandy Clark brought in Alan Milleron loan from Blackburn Rovers as cover. Later that same season, in which St Johnstone lost their Scottish Premier League status, Cuthbert was given a seven-game run of starts. Cuthbert started the 2002–03 season between the goalposts but lost it for a three-month spell after Main had recovered from his broken limb. Main however, was sold to Livingston and the management at St Johnstone then brought in Craig Nelson during the 2003–04 season to replace the gap left by Main. However Cuthbert's performances kept him in favour for all but seven games. When John Connolly brought in Rangers' young goalkeeper Allan McGregor on loan in 2004–05, Cuthbert had to settle for a place on the bench for the majority of the season. For the first part of the 2006–07 season, Owen Coyle opted to go with new signing Bryn Halliwell. Cuthbert's hopes of challenging the Englishman for the starting jersey were set back after the former broke his finger in training, an injury that required surgery. He returned to action in the new year, making his first start in a 2–1 win over Clyde on Boxing Day. On 31 March 2007, Cuthbert was given a straight red card in a 2–1 loss to Livingston at McDiarmid Park, resulting in his missing two out of St Johnstone's four remaining league games.
Greenock Morton
In May 2008, after ten years at McDiarmid Park, Cuthbert did not renew his contract with the club. Cuthbert went on trial at Queens before he joined Greenock Morton in August 2008. On 27 December 2008, Cuthbert received the second straight red card of his career when against Airdrie United following a poor back pass by Chris Smith he brought down the attacker, to conceded a penalty in a game Morton lost 1–0 at Almondvale Stadium. Cuthbert despite playing almost every game in the 2008–2009 season, found that Morton's first contract offer to be of an unacceptable nature. Towards the end of May, Cuthbert was tied down to a new two-year contract. He was released in May 2011, after the club had secured their First Division status for the next season.
Ayr United
After his release by Morton, Cuthbert signed for newly promoted Ayr United, whom he had been linked with in January.
Hamilton Academical
On 1 July 2012, Cuthbert signed for Hamilton Academical on a one-year deal. In August 2013, Cuthbert played his 300th first team game in a 1–0 Scottish League Cup victory over Kilmarnock. Cuthbert helped Hamilton gain promotion to the Scottish Premiership in 2013–14, but then turned down an offer of a new contract with the club.
Raith Rovers
Cuthbert signed for Raith Rovers in June 2014. He played his 400th game on 15 October 2016 in a 0–0 draw against Hibernian. A persistent groin injury forced Cuthbert to retire from playing in February 2018.
Coaching career
After he retired as a player, Cuthbert became a coach at Raith Rovers. He took caretaker charge of the team in September 2018, after Barry Smith resigned.
