Hasselbaink returned to the Premier League with Chelsea for a club record £15 million fee in May 2000, where he once again led the league in scoring during his first season, earning him a second Premier League Golden Boot. He also played in the 2002 FA Cup Final and helped Chelsea to a career high and then club record second-place Premier League finish in 2003–04. He moved to Middlesbrough on a free transfer in July 2004 and played in the final of the UEFA Cup in 2006. After being released at the end of the previous season, he signed with Charlton Athletic in July 2006, before joining Cardiff City in August 2007. He played on the losing side in the 2008 FA Cup Final before retiring from play at the end of the season.