Jimmy Floyd Hasselbaink

Jimmy Floyd Hasselbaink is a Dutch striker, born in Suriname, who scored 127 Premier League goals for Leeds, Chelsea, Middlesbrough and Charlton. He is the only player to have won the Golden Boot with two different clubs.

Clubs
Telstar, AZ Alkmaar, Campomaiorense, Boavista (1996 to 1997), Leeds United (1997 to 1999), Atlético Madrid (1999 to 2000), Chelsea (2000 to 2004), Middlesbrough (2004 to 2006), Charlton Athletic (2006 to 2007), Cardiff City (2007 to 2008)
Premier League
288 appearances, 127 goals
Honours
Premier League Golden Boot 1998/99 (shared) and 2000/01, Charity Shield 2000, Portuguese Cup 1997
International
Netherlands, 23 caps, 9 goals
Fantasy price
£10.0m in 2001/02

Who did he play for?

He scored 20 league goals for Boavista in 1996/97 and won the Portuguese Cup. Leeds paid £2 million for him that summer.

He scored 16 league goals in his first season and 18 in his second, sharing the 1998/99 Golden Boot with Michael Owen and Dwight Yorke. He also shared the most assists that season. After a contract dispute Leeds sold him to Atlético Madrid in August 1999 for £12 million, and he scored 24 league goals in a season that ended in relegation.

Chelsea paid a club record £15 million for him in 2000, equal to the British record at the time. He scored 22 minutes into his debut, the Charity Shield against Manchester United, the last club match at the old Wembley. He scored 23 league goals that season and won the Golden Boot outright, then 23 again in 2001/02.

He left Chelsea on a free in July 2004 with 69 league goals and scored 13 in his first season at Middlesbrough. He played in the 2006 UEFA Cup final, had a season at Charlton and finished with an FA Cup final for Cardiff in 2008.

He played at the 1998 World Cup for the Netherlands. Since retiring he has managed Royal Antwerp, Burton Albion twice, QPR and Northampton, and was an England assistant coach from March 2023 to August 2024.

The moment: Coventry, 21 October 2000

Stamford Bridge, Saturday 21 October 2000. Chelsea 6-1 Coventry City, Claudio Ranieri's first weeks in charge.

Hasselbaink won a penalty on 25 minutes and scored it. Before half-time he cut in from the left and bent one in. After the break he tapped in after Gianfranco Zola's shot was saved, then finished with his left foot: four goals in 33 minutes. Zola and Tore André Flo scored the others.

He was the second Chelsea player to score four in a Premier League game, after Gianluca Vialli.

Why the streets won't forget

The name came from a chairman at Campomaiorense in Portugal, who told the press the club had signed a player called Jimmy. It stuck.

Some Leeds fans called him Jimmy Floyd Piggybank after the contract dispute that ended with his sale to Atlético.

Asked why he joined Chelsea, he told the club's website they were gagging for a number nine.

He won the League Two title as Burton's manager in 2015, was on Strictly Come Dancing in 2025, and was named Suriname's assistant coach in December 2025.

Which seasons can you draft him in?

Nine. 1999/2000 was in Spain.

SeasonClubPriceHis real league seasonVerdict
1997/98Leeds United£8.5m33 games, 16 goals, 6 assistsPick him
1998/99Leeds United£10.5m36 games, 18 goals, 13 assistsPick him
2000/01Chelsea£11.5m35 games, 23 goals, 9 assistsPick him
2001/02Chelsea£10.0m35 games, 23 goals, 6 assistsPick him
2002/03Chelsea£8.0m36 games, 11 goals, 7 assistsWorth a look
2003/04Chelsea£8.5m30 games, 12 goalsWorth a look
2004/05Middlesbrough£9.0m36 games, 13 goals, 7 assistsWorth a look
2005/06Middlesbrough£6.5m22 games, 9 goalsLeave him out
2006/07Charlton Athletic£5.5m25 games, 2 goalsLeave him out

Four straight seasons worth picking. The best value is 2001/02: the same 23 goals as the year before for £1.5m less.

Want him in your retro fantasy football team for 2001/02? He'll cost you £10.0m.

Draft a squad from 2001/02