Rochemback made his league debut in a 2–1 home win over Arsenal on 10 September, and scored his first goal on 11 February 2006 in a 3–0 victory against leaders and reigning champions Chelsea also at the Riverside Stadium. His first FA Cup goal for Middlesbrough came direct from a free kick, in a 4–2 victory over Charlton Athletic in a quarter–final replay on 11 April. He also played an important role in Middlesbrough's run to the 2006 UEFA Cup Final in a 4–1 victory (4–3 on aggregate) against FC Basel in the quarter–final second leg on 6 April, which he was named man of the match.