On 22 September 2009, Degen started in Liverpool's 1–0 League Cup win against Leeds United at Elland Road. In the next round of the same competition, he started against Arsenal in a 2–1 defeat for Liverpool. Degen got his first Premier League start in an away match against Fulham on 31 October 2009, in place of the injured Glen Johnson. He was subsequently sent off for a foul on Clint Dempsey in the 79th minute of the 3–1 defeat. Following another injury to Glen Johnson, Degen featured more in the Liverpool team, both at right back and on the right of midfield. After a 2–0 defeat of Tottenham Hotspur, Degen expressed his pleasure with the win and his performance, saying "I think I can improve a lot. I haven't had the best of luck with injuries during my time with Liverpool and I know there is still more to come from me. I have only played at around 60 per cent of my potential and hope I can show much, much more.". On 10 February 2010, Degen started the game against Arsenal at the Emirates Stadium. On 19 April 2010, Degen played the last 13 minutes of the home 3–0 win versus West Ham United at Anfield.