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After the Town’s successful League Two campaign in 2011/12, Roberts was one of Town boss Paolo di Canio’s first signings during the close season - his arrival having helped Huddersfield to promotion the previous season widely seen as a coup - the wide man confirming that he had turned down an offer from a Championship club to sign for Swindon. Persistent leg injuries interrupted Roberts’ pre-season programme and kept him out for the first month of the season - his first game not coming until Swindon visited Carlisle in mid-September, Cumbrians boss Greg Abbott admitting that he had tried to sign Roberts before he had joined the Town, but he couldn’t even come close to the salary that the winger had agreed to at the County Ground, branding his wage “ridiculous”. Though he generally impressed on his début after coming on as a second half substitute, boss di Canio was quick to state that he didn’t want his new wideman to play “tippy tappy” football - a quote that would follow Roberts during his time at Swindon.
After making his full début at Portsmouth three days later, Roberts started the next two games, but was dropped to the bench for the trip to Shrewsbury at the end of September - before a groin problem kept him out of the next two games. When he did return to action in mid-October, he netted his first in Swindon colours - the Town’s opening goal as they came back from two behind to draw with Coventry - soon after, Roberts admitted that the start of his Swindon career had been a “nightmare” in terms of injuries.
Unfortunately, Roberts never really managed to win over the Swindon fans - during November, di Canio substituted the winger in every game except one, a home defeat to non-league Macclesfield in the FA Cup, which the Italian branded Roberts’ first half performance as “pathetic” - and by the end of the month, Roberts was dropped to the bench where he would remain until the end of the year - the Town boss preferring Raffa de Vita on the left side, as Swindon played some of their best football of the season. For his own part, Roberts was very open that he had not lived up to expectations at the County Ground, stating that he hadn’t played well consistently, and probably did not deserve to be in the team, but that he had “half a season to put things right, to prove to myself and prove to the manager that I’m good enough to play for the team.”
Roberts returned to the starting eleven in the New Year - playing the full ninety minutes of a 4-0 win over Carlisle, but though he performed well, he admitted to being frustrated to have not found the net - soon after, the winger revealed that a private chat with boss di Canio had given him encouragement to regain his form. Roberts started the following two games, before being dropped to the bench for a trip to Leyton Orient - but when fellow wideman Matt Ritchie was sold to Bournemouth out of the blue the following day, with the Town in the middle of a takeover deal, Roberts’ first team opportunities completely opened up, and he was virtually ever-present for the remainder of the season.
Though Roberts described Paolo di Canio’s potential departure as “the worst thing in the world”, Ritchie’s sale prompted a chain of events that would see the Italian depart the County Ground - his final instruction to his backroom staff was his lineup for the top-of-the table clash at Tranmere, in which Roberts took a starring role. After Swindon took the lead early in the second half through James Collins, Roberts doubled the advantage with twenty minutes left on the clock, with an exquisite half-volley from the edge of the area - then, with the entire Tranmere team pushing forward for an equaliser after pulling a goal back, Roberts scored with a truly incredible half-volley from well inside his own half - fully seventy yards - Rovers keeper Owain Fon Williams caught miles off his line, and unable to scramble back to claw it away. The victory took Swindon to the top of the League One table, and as the away support sang Roberts’ name during the post-match celebrations, with his team-mates congratulating him, it looked as though Roberts had finally announced his arrival.
Though Roberts started all but one of the Town’s remaining games, under new boss Kevin MacDonald they faded out of the automatic promotion race, and Roberts only netted once more - in the penultimate game of the regular season in a 3-0 win over Stevenage that secured Swindon’s place in the play-offs. Roberts’ form continued to blow hot and cold, and with the more dynamic Ritchie now departed, a section of the Town support often vented their frustration on his replacement. Roberts didn’t miss a minute of the play-off campaign, appearing in both the home and away legs against Brentford - but unfortunately, though he swung in the corner from which Aden Flint netted a dramatic last gasp equaliser in the second leg at Griffin Park, his most memorable contribution was an awful square pass straight into the path of Bees striker Clayton Donaldson, who ran fifty yards before dinking the ball over Wes Foderingham in the Town goal, to give Brentford a 3-1 lead early in the second period. Though Roberts netted the last penalty in the resulting shootout, it was all in vain - Miles Storey’s earlier miss ensuring that it would be the hosts who progressed to the Wembley final.
Over the summer, when the new Town board slashed the playing budget by almost 50%, it always seemed likely that Roberts would be likely to be leaving the club - and almost as soon as the season was over, interest was rumoured from Chesterfield and Bradford. At first, it seemed that his high wages might scupper any potential deal, but after initial talks with Chesterfield, he agreed a deal to be released from his Town contract in June - the following day, he was unveiled by the League Two club, signing a three year deal - Spireites chief executive Chris Turner stating that he didn’t think there was “anybody outside the Premiership who is better on the left wing”.
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