subsequently left out of the starting lineup for four matches until Swindon faced Wolverhampton Wanderers in the League Cup second round, which they lost 6–5 on penalties following a 0–0 draw after extra time. Cuthbert scored his first goal for Swindon four days later in a 2–1 win at home to Southend United. Towards the end of the season, Swindon were well-placed for promotion to the Championship, but with only one win in their last six matches, the club finished in fifth place and would have to contest the play-offs. Swindon defeated Charlton 5–4 on penalties after their two-legged semi-final ended 3–3 after extra time. Cuthbert later said the success of getting to Wembley Stadium in his first season with the club was a dream come true. The play-off final saw Swindon lose 1–0 to Millwall, preventing the club from gaining promotion to the Championship. At the start of the 2010–11 season, Cuthbert was named as the club's vice-captain. He scored his first goal of the season in a 2–1 defeat away to Milton Keynes Dons on 28 August 2010. Six months later, Cuthbert scored his second goal of the season in a 2–1 defeat away to Colchester United on 12 February 2011. In March, Cuthbert suffered a fractured cheekbone in a 1–1 draw with Dagenham & Redbridge, but was told he did not need surgery. Swindon were relegated to League Two after a 3–1 defeat away to Sheffield Wednesday on 25 April. Following the completion of the season, Cuthbert reflected on a mistake he made during a 2–1 defeat at home to Notts County, two days before Swindon were relegated, and was intent on returning the following season as a better player. However, Cuthbert was not offered a new contract, despite expressing a desire to remain with the club. Leyton Orient Ahead of the 2011–12 season, on 3 June 2011, Cuthbert signed a two-year contract with League One club Leyton Orient. He made his Leyton Orient debut on the opening day of the campaign, playing as a centre back in a 1–0 defeat to Walsall. Cuthbert received a red card in a 3–1 defeat at home to AFC Bournemouth on 13 September 2011 and was subsequently suspended for three matches. Cuthbert scored his first goal for the club on 8 October in a 3–2 win over Scunthorpe United. At the end of October, Cuthbert was nominated for the League