Born in Suriname, he and his family would later move to the Dutch city of Zaandam where he first played football, initially as a goalkeeper, later transitioning to the role of a right winger and finally a forward.

He was signed by English side Leeds United for a £2 million fee before the 1997–98 season, where he established himself as a prolific goalscorer and went on to win the Premier League Golden Boot award in 1999.

[13] He had an unsuccessful trial with FC Eindhoven, and after failing to agree terms with PEC Zwolle he instead spent the 1993–94 season training with HFC Haarlem.

[14] He then played amateur football for Neerlandia whilst he looked abroad for a professional contract, spending time in Austria with Admira Wacker.

[15] Hasselbaink signed for newly promoted Portuguese Primeira Divisão side Campomaiorense in August 1995 after impressing trainer Manuel Fernandes on a trial.

[22] He scored on his Premier League debut in a 1–1 draw with Arsenal at Elland Road on 9 August, though initially he struggled to adapt to the pace of the English game.

[32] Despite this, Hasselbaink shared the league's Silver Boot award with Catanha (Málaga CF), scoring only three goals fewer than top-scorer Salva Ballesta (Racing de Santander).

[33] Atlético reached the final of the Copa del Rey at the Mestalla Stadium but lost 2–1 to Espanyol; Hasselbaink scored a late consolation goal.

[36] Hasselbaink later stated he was "dismayed" at Vialli's dismissal and that the players hated Ranieri and fitness coach Roberto Sassi's running-focused training methods.

At the start of the 2001–02 season, Hasselbaink earned the distinction of scoring the first competitive goal at Southampton's new St Mary's Stadium as Chelsea won 2–0 on 25 August.

[41] Hasselbaink was a doubt for the final due to a hamstring injury, and was substituted on 68 minutes at the Millennium Stadium as Chelsea lost 2–0 to rivals Arsenal.

[44] Ranieri initiated a squad rotation system for the 2002–03 season but focused the team around Gianfranco Zola, which limited Hasselbaink's playing time.

[50] In the 2003–04 season, he scored 17 goals in all competitions, which, despite the arrival of new strikers Adrian Mutu and Hernán Crespo, made him top-scorer at the club for the third time in four years.

[57] In the 2004–05 season he finished as the club's top-scorer with 13 goals in 36 Premier League games, including a hat-trick in a 4–0 win over Blackburn Rovers at Ewood Park on 16 October.

[68] Manager Dave Jones said that Hasselbaink initially took time to settle and become match fit but despite being a demanding player his professionalism was ultimately a positive influence.

[73] Hasselbaink came to the attention of Netherlands manager Guus Hiddink whilst playing in England for Leeds United and made his international debut on 27 May 1998 in a 0–0 draw in a friendly with Cameroon at the GelreDome in Arnhem; he came on as a 61st-minute substitute for Marc Overmars.

[74] He was part of the Dutch squad for the 1998 FIFA World Cup in France, as back-up to established international strikers Patrick Kluivert, Dennis Bergkamp and Pierre van Hooijdonk and wingers Boudewijn Zenden and Marc Overmars.

[74] With other strikers not fully fit, Hasselbaink started the opening game against Belgium at the Stade de France, but missed a scoring opportunity in the 0–0 draw and was taken off for Bergkamp after 65 minutes.

Hasselbaink scored against Spain in a 2–1 win at the Estadio de La Cartuja on 15 November 2000 but both he and Spanish captain Fernando Hierro were sent off for fighting late in the game.

On 21 August, he came on as a substitute in a 1–0 win over Norway at the Ullevaal Stadion, and on 7 September he scored in a 3–0 victory over Belarus, the opening game for Euro 2004 qualifying; this was his last appearance for Netherlands.

[85] Tom Sheen, sports reporter for The Independent and a Chelsea supporter, wrote that "[Hasselbaink] possessed one of the best strikes ever seen at Stamford Bridge, was an expert free-kick taker, great with both feet and decent in the air".

[100] Two weeks later, Burton came from 2–1 down, with ten men following the dismissal of goalkeeper Jon McLaughlin, to defeat Cambridge United 3–2 at the Abbey Stadium and win the League Two title.

[103] On 4 December 2015, Hasselbaink was appointed as manager of Championship club Queens Park Rangers; he signed on a rolling contract, alongside his assistant David Oldfield.

[106] Despite the sale of leading scorer Charlie Austin earlier the same day, Hasselbaink earned his first win in charge of the "Hoops" on 16 January 2016, a 3–0 victory at Rotherham United.

[109] On 4 September 2017, Hasselbaink was appointed manager of League One club Northampton Town on a three-year deal, replacing Justin Edinburgh who had been sacked after four losses from the start of the season.

[116] He resigned as Burton Albion manager on 5 September 2022 with his team sitting bottom of the table with one point out of seven games, claiming that he had "taken the club as far as I can with the limited resources available".

[118] In August 2024, following Southgate's departure in the aftermath of England's UEFA Euro 2024 final defeat, Hasselbaink also departed his role as assistant head coach.

[122]Shortly afterwards, Port Vale chairman Norman Smurthwaite revealed that he had rejected Hasselbaink for the vacant managerial position at his club in 2014, out of fear that racist elements of their support would abuse him.

[123] On 28 September 2016, Hasselbaink was named and shown in The Daily Telegraph's sting operation involving exposing football management personalities engaging in improper conduct.

[124] Queens Park Rangers launched an internal investigation and went on to release a statement fully backing Hasselbaink and stated that The Daily Telegraph failed to provide sufficient evidence regarding their sting operation.