 Rambai muchinyora ndima iyi - Hasselbaink akadzokera kuPremier League neChelsea nokuda kwechikwata che 15 mamiriyoni emadhora muna May 2000, apo akatungamirira zvakare mukukwikwidza mumutambo munguva yake yokutanga, achimuwana wechipiri wePremier League Golden Boot. Akatambawo mu2002 FA Cup Finaluye akabatsira Chelsea kusvika pakakwirira yebasa uye ipapo rekodhi yekirabhu yechipiri-chinzvimbo Premier League kupedzisa muna 2003 04. Akatamira kuMiddlesbrough pane imwe nzvimbo yakasununguka munaJuly 2004 uye akatamba mumagumo eEFAFA Cup muna 2006. Mushure mekusunungurwa pakupera kwemwaka wapfuura, akasaina neCharlton Athletic muna Chikunguru 2006, asati ajoina Cardiff City muna Nyamavhuvhu 2007. Akatamba parutivi rwekurasikirwa mu2008 FA Cup Final asati aenda pamudyandigere pakupera kwemwaka. 