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A Scotland B international defender who signed for the Town from Celtic in July 2009 for an undisclosed fee, despite interest from both Scottish Premier and Championship clubs - manager Danny Wilson admitting that he had been chasing Cuthbert for over a year, stretching back to his previous tenure at Hartlepool. After his recovery from a hernia operation sidelined him for most of the pre-season build up, by his own admission he gave an awful debut performance on the opening day at Gillingham, lining up on the right side of defence in a 5-0 defeat, and he was dropped to the bench for the next four games, returning to action at the expense of Sean Morrison in a central position for the Carling Cup tie at Wolves. After the Town held the Premier League outfit to a 0-0 draw, succumbing only on penalties, Cuthbert kept his place in the side for the following Saturday’s match against Southend, and he scored a goal on his home debut in a 2-1 win.
From that point on, Cuthbert was one of the Town’s most consistent performers, as his partnership with Gordon Greer at the heart of the defence proved to be a solid base for a promotion push - Cuthbert’s next absence from the side wasn’t until March, when a knee injury sustained in a superb 1-0 win at Southampton forced him off in the first half. A scan revealed that initial fears of ligament damage were unfounded, and though Cuthbert missed the following game and was benched for the trip to Hartlepool, he returned to the starting line-up for an outstanding 3-0 win at Elland Road, that catapulted the Town into the second automatic promotion spot over Leeds. When the Town dropped points in four consecutive games in April, and after a defensive mix-up involving Cuthbert led to a goal against Walsall, it appeared that he was suffering from tiredness - perhaps as a result of his lack of pre-season training -Wilson dropping him to the bench for the final two matches of the season against Brentford and Millwall. He returned to action for the play-off campaign, as the Town narrowly missed out on promotion, losing 1-0 to Millwall at Wembley. Before the new season started, Cuthbert was installed as the club's new vice captain after Greer's departure for Brighton.
With Greer gone, Cuthbert started the season as the obvious first choice centre-back - the initial problem appearing to be who to pair him with - and after his partnership with Lecsinel Jean-François brought two defeats and a draw with six goals conceded in the Town's first three games, the problem looked to be rectified in September with just one goal conceded in five games once Sean Morrison was installed alongside him. Going into October though, the defence became more and more leaky - prompting manager Wilson to bring in Andy Frampton from Millwall on loan. At first, Frampton's arrival saw Cuthbert move out to a right-back position, and when Frampton's loan was cut short by injury, Cuthbert initially remained on the right side, with Jean-François and Morrison paired in the middle - a 1-0 defeat at Notts County in mid-November though changed Wilson's mind again, and Cuthbert was restored to his usual central position. When Frampton returned to the fray at the turn of the year, Cuthbert was paired with him at the heart of the defence for the first time - but when that failed to bring positive results in two games, Cuthbert found himself dropped to the bench for the first time in the season.
Cuthbert returned to the starting eleven just two games later, in mid-January, after Frampton was again sidelined by injury, and Morrison was sold to Reading. The partnership with Jean-François this time brought another two defeats - and Frampton's return saw Cuthbert paired with him again - bringing two clean sheets in as many games (though unfortunately Swindon failed to score at the other end) - but when the Town conceded another three goals, this time at Bournemouth, Cuthbert was again dropped, this time in favour of Aden Flint, who Wilson had signed from non-league Alfreton. A 3-0 defeat at Leyton Orient prompted Wilson to change things around yet again - and Cuthbert returned to the fray, scoring an equalising goal at Colchester which looked to have given the Town a point in a game they largely dominated - only to succumb to an injury time defeat. By now, the Town's winless run had stretched to nine games - and Cuthbert and Frampton remained at the heart of the defence for the next eight matches, despite the Scot sustaining a fractured cheekbone in March against Dagenham - an injury which at first was reported to require surgery, until a scan allayed those initial fears. The settled back line had little effect on the Town's performances though, and still they remained winless - during a period where Wilson resigned and was replaced with Paul Hart at the helm, with Swindon deep in relegation trouble. After successive defeats at Brighton and Exeter at the end of March (the latter being a particularly poor performance), Hart decided to drop Cuthbert to the bench once more - only returning towards the end of April, when Frampton was injured again. On his return, Cuthbert made an awful mistake - having been played into trouble by Michael Rose, he was caught in possession of the ball allowing Lee Hughes through to score a winning goal against Notts County, after the Town were winning and in control of the game right up until the final twelve minutes - the goal all but confirming Swindon's relegation to League Two, and prompting some of the most depressing scenes ever witnessed at the County Ground, with fans jeering the players and shouting abuse at the manager. Cuthbert himself later stated that it was a mistake that haunted him - and Hart again dropped him to the bench for the following weekend's match at Sheffield Wednesday - only to come on as a first half substitute for the again injured Frampton - Hart later blaming Cuthbert for missing a ball into the area that resulted in Wednesday's third goal, as defeat finally made relegation a mathematical certainty, and Hart was relieved of his position as manager. With Frampton out, caretaker boss Paul Bodin included Cuthbert in his side to play out the final games of the season.
Those games proved to be Cuthbert's last in a Town shirt. With his contract up for renewal, Swindon did have an option to renew for a further year - but with no manager in place, no decision was made to trigger the deal, with reports that the club wanted to renegotiate the deal following relegation. At the end of May, Paolo di Canio was appointed as Town boss, but no contract offer was immediately forthcoming - and Cuthbert decided to join Leyton Orient on a two year contract.
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