Having caught the eye of Middlesbrough manager Steve McClaren during a UEFA Cup game for Sporting earlier in the year, Rochemback signed a five-year deal with the Teesside club on transfer deadline day of 31 August 2005. The late deal had been jeopardised by financial complications: Sporting were subject to a €1 million payment to Barcelona if Rochemback did not spend three years on loan at the club, so Middlesbrough agreed to pay this fee as well. This transfer is one of those about which the Stevens inquiry report in June 2007 expressed concerns because of the lack of co-operation from agents Pini Zahavi and Barry Silkman.