|view Benson's match-by-match record|
After originally agreeing to join the Town on a loan deal in November 2011, only for the move to be rejected by the Football League as it wasn't registered with them until seven minutes after the transfer deadline, Benson agreed a permanent two-and-a-half year deal the following month - moving to the County Ground from Charlton when the window reopened in January, in an exchange deal with Leon Clarke.
Lacking match fitness, Benson made his debut as a second half substitute with the Town drawing 0-0 with AFC Wimbledon - two minutes after his introduction, Swindon took the lead and they went on to win 2-0, with Benson making a good initial impression with his aerial ability and his running the channels, though Town boss Paolo di Canio referred to him as "Mr Rustyman" after he had squandered a couple of chances. The following weekend though, Benson made even more of an impact - his image plastered all over the back pages of the Sunday papers after scoring the winning goal in a 2-1 victory over Premier League Wigan - though in truth, the goal had more than an element of luck - Benson deflecting Matt Ritchie's long range effort past keeper Ali Al-Habsi.
After making his full debut in a 2-1 win at Rotherham in mid-January, Benson marked his full home league bow with the winning goal in a drab victory over Macclesfield - his arrival in the Town team at the beginning of a superb ten match winning run in the league. The striker hit a purple patch in February - hitting seven goals in eight league matches, notching his hundredth career goal in the process, and winning the League Two Player of the Month award. It was also a month in which Swindon won through to the Johnstone's Paint Trophy final, and moved to the top of the League Two table. Boss di Canio soon stated that he wouldn't swap Benson for any other striker in the division.
After defeat at Wembley though, di Canio rested the front man for the first time since his arrival, with Benson suffering from a slight neck injury, he was benched for the visit of Bristol Rovers - when he returned to action for the busy start to April, Benson netted a crucial winner at Morecambe. Over the coming weeks, Swindon edged nearer to promotion with victories over Northampton and Plymouth - but when promotion was finally assured despite a 3-1 defeat at Gillingham, Benson was kept out with a tight hamstring. He made up for it the following weekend though - hitting two goals in a 5-0 demolition of Port Vale that wrapped up the League Two title, goals that also took him clear as the Town's leading League goalscorer of the season, until Alan Connell also netted his eleventh of the campaign with five minutes remaining.
Though James Collins and Andy Williams signed over the summer, Benson opened the 2012/13 campaign with a goalscoring start - finishing off a training ground free-kick routine for the first goal in a 3-0 win over Championship side Brighton in the League Cup. Soon though, di Canio began to rotate his striking options, and after injury kept him out of matches against MK Dons and Stoke, plus the arrival of another front man, Adam Rooney, on loan from Birmingham - Benson found his first team opportunities more limited, despite goals against Carlisle and Burnley.
When injury to Williams gave Benson a chance in mid-October though, the striker failed to seize the opportunity in the eyes of his manager against Coventry, who criticised his lack of commitment to not follow up a header from Matt Ritchie that had bounced off the post - a game in which Benson was substituted with the Town 2-0 down - his replacement Collins netting an equalising goal with ten minutes remaining. The following weekend, when defender Aden Flint was sent off in the first half against Scunthorpe, Benson was the man to make way - and when former youth team striker Miles Storey netted goals in back-to-back games against Stevenage and Aston Villa, after starting five games in the month, in November he found himself out of the first team picture.
In the middle of the month, di Canio strengthened his attacking options further still - signing Chris Martin on loan from Norwich - and at the same time, it was revealed that Benson was holding talks with Portsmouth about a loan move - the striker signing an initial one month deal, which was later extended to two. When Benson’s loan spell was coming to an end, though it appeared he wanted to remain at Fratton Park, Pompey’s well documented financial problems prevented them from pursuing him - and Town boss di Canio confirmed that Benson had received a “very good opportunity” of a two year deal at a promotion chasing League Two club, that he suggested the striker should accept. The offer was later revealed to have come from Bradford, but Benson initially turned them down to stay at Pompey - and when he did return to the County Ground, he also turned down the opportunity to join Cheltenham on loan with a view to a permanent transfer. Rumoured interest from Bristol Rovers also came to nothing, before the Cheltenham deal was revived - and at the end of January, he moved to Whaddon Road until the end of the season, where he played out an unsuccessful play-off campaign.
While he was away, there were huge changes at the County Ground - with a new board installed and di Canio having left the club, Benson admitted that he thought his time at Swindon was over, and that he was looking forward to proving himself under new boss Kevin MacDonald - but though the new Town boss reportedly told Benson he was going to be part of his plans for the new campaign, it was later revealed that he had been offered to rivals Oxford, as the new board attempted to slash the wage bill. When chairman Jed McCrory was questioned by fans on social media site Twitter over the move, he openly questioned Benson’s goalscoring record in return - and when the Town’s pre-season campaign started, it was obvious that the striker wasn’t going to get much of a look-in to the Town’s new look squad - being played at centre back for a friendly at Supermarine. Benson soon confirmed that he had been told he could move on but with a year left on his contract, he was under no pressure to rush into a decision - and three weeks into the new campaign, he finally joined Conference outfit Luton on a season long loan.
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