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A left-sided Irish U21 international, initially signed on a month's loan from Leeds on the loan transfer deadline day in November 2009, and after a previous appearance at the County Ground the season before had resulted in an early bath when he was sent off for a two footed challenge for United - Sheehan's debut for Swindon looked to be going the same way, when, already booked, manager Danny Wilson substituted him as the FA Cup tie at Wrexham turned into a fiery encounter in the second half. Sheehan’s opening few games for the Town came on the left side of midfield, but he reverted to his more usual left back role after a 3-0 defeat at Bristol Rovers in December - becoming an important part of the Swindon side that was challenging for promotion, both defensively and with his set piece delivery. He was perhaps unlucky not to score with one of his curling free-kicks, the closest he came was rattling the underside of the crossbar with an effort against Brighton.At the turn of the year, the Town agreed to extend his loan deal until the end of the season, and with Sheehan being frozen out at Leeds, it seemed likely that the switch may become permanent.
After a hamstring strain picked up against Gillingham in January kept him out for five weeks, after he returned in February, the only match he missed in the run-in was against parent club Leeds, though in truth his form seemed to dip towards the end of the season. He finally opened his goalscoring account with a cool finish to equalise in a 2-2 draw at Wycombe in April, and though he started the first leg of the Play-Off semi-final against Charlton, he missed the return game with a hip injury, that threatened to rule him out of the final. With captain Gordon Greer suspended, Sheehan was rushed back to action - returning to training the day before the big game, and he managed just over an hour before being withdrawn, as the Town were defeated by Millwall. After admitting that he wasn’t fully fit for the game, Sheehan was coy about whether he would be returning to Swindon - and when Wilson signed full-back Michael Rose in June, it was confirmed that Sheehan would not be returning.
It therefore came as somewhat of a surprise when, two months later on transfer deadline day, after Rose had not had the best of starts in a Town shirt and Sheehan had not yet found a club, he returned to sign a one-year deal - stating that he had unfinished business at Swindon, and he wanted to fulfill his dream of playing in the Championship. Sheehan returned a few days later, coming on as a second half substitute in a 0-0 draw at Carlisle, but he had to wait another two weeks before making the starting eleven, and he did so in style, notching the Town's first goal in a 2-1 win at Walsall.
A fortnight later, Sheehan retired from a match against Plymouth after just fifteen minutes with a hamstring strain (with the Town already 2-0 down) - an injury that kept him out of action for a month - then, when he made his comeback, he was sent off against Leyton Orient for serious foul play - a decision that prompted Danny Wilson to vent his anger at referee Trevor Kettle. When he returned from his three match ban, Michael Rose was in possession of the shirt, and it wasn't until the Christmas period when Sheehan started a match again - the two players both in and out of the side during January, with Sheehan benched for most of February after gifting a goal to Bristol Rovers in a local derby between the two relegation haunted clubs - by the end of February, Sheehan was completely out of the first team picture - the Irishman stating that it was the most frustrating season of his career.
After Wilson resigned at the end of the month, new boss Paul Hart finally named Sheehan in the starting eleven for a crucial relegation encounter with Dagenham in mid-March - and he went on to feature in the next eight games, as Swindon slid down to the bottom of the table. His final appearance in a Town shirt came in a depressing home defeat to Notts County that all but sealed the Town's relegation in an awful County Ground atmosphere - the following weekend, Sheehan sat out the defeat at Sheffield Wednesday that confirmed the inevitable demotion, and Hart was sacked shortly after. Before the season was out, Sheehan was blasted by caretaker boss Paul Bodin for arranging a trial with Preston - Bodin refusing to pick the defender for the final two games of the season - Sheehan eventually signing for Notts County on a two year deal.
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