[3] Benson's first season with Dagenham was frustrating as he was not a regular first-team player, scoring only one Conference National goal, and was out for three months with a broken leg.
Notts County made a bid to sign him, which Charlton accepted, although the move collapsed after they failed to agree personal terms.
Benson's first goal for Swindon came when he scored the winner in their FA Cup third-round victory over Premier League team Wigan Athletic, although replays showed he was in an offside position.
Benson's goalscoring form was rewarded on 9 March 2012 when he was named League Two Player of the Month for February after scoring five goals in five matches and being widely praised by manager Paolo Di Canio.
[19] Benson scored his first goal for the club on 12 February, tapping the ball past goalkeeper Paul Smith in another 2–1 victory, this time against Southend United.
[21] On 26 August 2013, Benson signed for Conference Premier club Luton Town on a season-long loan, with the possibility of a permanent transfer taking place in the summer of 2014.
After his successful loan spell at Luton during the 2013–14 season, Benson signed a permanent two-year contract with the club on 22 July 2014.
[31] Benson re-signed for Dagenham & Redbridge who were newly relegated into the National League, on an initial one-year contract on 6 August 2016.
[34] Benson played in both legs of the play-off semi-final defeat to Forest Green Rovers, losing 3–1 on aggregate,[35][36] and finished the season with 37 appearances and six goals.
[43] From the summer 2019, he was hired as assistant to professional development phase lead coach, Dan Walder, helping with the U16s and U18s on a daily basis.