One Player of the Month award. Cuthbert suffered a hamstring injury on 31 March 2012, in a 2–0 defeat to Charlton Athletic, causing him to miss the final seven matches of the season. Despite his injury, Cuthbert was named Leyton Orient's Player of the Year for the 2011–12 season. Shortly after receiving it, Cuthbert said that winning the award was a proud moment for him. Cuthbert made a recovery from his injury ahead of a friendly match with Ebbsfleet United in pre-season ahead of the 2012–13 campaign. After just two appearances, Cuthbert again suffered a hamstring injury that kept him from playing until December 2012. In the Football League Trophy southern section semi-final at home to Yeovil Town, Cuthbert provided a winning assist for Dave Mooney in a 1–0 win to send the club through the southern section final. In a 0–0 draw with Preston North End on 23 March 2013, Cuthbert suffered a fractured metatarsal that caused him to miss the rest of the season. Shortly after the end of the season, Cuthbert signed a new two-year contract with the club. Cuthbert played most of the 2013–14 season at right back, as Leyton Orient came close to promotion to the Championship, ultimately losing on penalties to Rotherham United in the play-off final. Cuthbert played in 54 matches in all competitions over the season, scoring four goals. The 2014–15 season was a complete contrast, as Leyton Orient were relegated on the final day of the season after only managing a 2–2 draw with Cuthbert's former club Swindon Town. After the season ended, Cuthbert was not offered a new contract. Following his departure, Cuthbert stated that the club told him to wait by the phone to find out if he would be offered a new contract upon the expiry of his deal, which he "wasn't set on waiting about to be told whether I was wanted or not". Luton Town Cuthbert signed a two-year contract with League Two club Luton Town on 26 May 2015. Upon his arrival, Cuthbert stated "The aim is promotion – I wouldn't have come to this club if I didn't think that was possible." He made his debut for the club on the opening day of the 2015–16 season in a 1–1 draw with Accrington Stanley. Cuthbert was sent off in second half stoppage time for a professional foul during a 3–2 defeat away to Notts