The former Whites striker left Elland Road for Atletico Madrid in 1999 and, 20 years on, he has given his side of the story.
During his time at Leeds, Hasselbaink made 73 appearances for the club, scoring 35 goals and registering three assists.
However, his good relationship with the fans was damaged amid his move to Atletico Madrid two years after joining the English club.
Hasselbaink, who at the time had two years to run on his Leeds contract, was reported by The Independent to "have put in a transfer request... after refusing to sign the best contract in the club's history."
The 1999 news article also stated that the move happened "amid many unsavoury and conflicting words", which seemingly paints a picture of how the forward's time at Leeds didn't come to the best of conclusions.
Speaking to the Sky Sports News Transfer Talk podcast this week, Hasselbaink appeared to point the finger at David O'Leary, who replaced the Tottenham-bound George Graham, for why his time at Elland Road ended sourly.
"I think he didn't see me in his long-term future at the club," said Hasselbaink. "We were in contract talks and it was not like he did his best to keep me.
"The things that went around when I left - he could have prevented all of those things. But it wasn't. I left with a bitter taste in my mouth."
Hasselbaink has claimed that he would not have left Leeds had Graham remained in charge, and expressed regret at how his time at Elland Road came to an end.
"I definitely think that if George Graham would have stayed then he would have never let me go," he added. "I left with a lot of negativity. I think it could have and should have been a lot better."
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