After a 4–0 home defeat to Aston Villa, he was captured on camera in tears and had to be consoled by captain Gareth Southgate. However, after this game the team went on to win seven out of their next eight games, advancing to the quarter-finals of both the FA and UEFA cups and defeating Premier League champions Chelsea 3–0, only their second league defeat of the season. Cattermole scored his first league goal for Middlesbrough on 2 April, in a 1–0 victory away at Manchester City, and played for Middlesbrough in the 2006 UEFA Cup Final.