5. Jimmy Floyd Hasselbaink – 2 Golden Boots
Jimmy Floyd Hasselbaink makes the list with 2 Premier League golden boot awards, one come while playing for Leeds the other came while playing for Chelsea.
He won his 1st Premier League golden boot in 1999 when he scored 18 goals in 36 appearances. The 2nd was with Chelsea in 2001 after scoring 23 goals for Chelsea in 35Premier League appearances.