Signed by Leeds in 1997 from Portugese club Boavista for £2 million, Jimmy went on to win the Premier League Golden Boots award for the 1998-99 season. From there he was sold to Athletico Madrid for £10 million. His sole season there was a strange one, which saw him reach the Copa del Rey final whilst simulataneously suffering relegation, That summer he was bought by Chelsea for a then club record fee of £15 million. He returned to the Premier League on fine form, earning his second Golden Boot by scoring 23 league goals. Unfortunately he was unable to win any silvereare at Chelsea, losing out in the 2002 FA Cup Final. He moved to Middlesbrough on a free in 2004 and helped them come runners-up in the 2006 UEFA Cup Final. After retiring Jimmy went on to manage Antwerp, Burton, QPR and Northampton.