Jose Mourinho and Jimmy Floyd Hasselbaink reportedly crossed paths just once when the Portuguese took charge at Stamford Bridge, with the forward soon leaving the club—a move Mourinho would later admit he regretted.
During his first year in charge, Mourinho delivered Chelsea’s first league title in half a century, backed by a squad that had plenty of attacking options.
Didier Drogba and Eidur Gudjohnsen led the line, while Frank Lampard was starting to establish himself as a real threat from midfield.
Mourinho told Hasselbaink he regretted letting him leave Chelsea
Hasselbaink, who had joined Chelsea in 2000, found himself surplus to requirements despite a strong stint with the club.
Speaking on ‘Clutch 9,’ the Dutchman shared that Mourinho later admitted it had been a mistake to move him on. The striker ended up at Middlesbrough, where he continued to perform well.
Reflecting on that period, Hasselbaink said: “So he still had four strikers and he must have thought Kezman is better than Hasselbaink or whatever.”
“He never spoke to me, never said anything. Afterwards when I left Middlesbrough and I did well at Middlesbrough, he did say ‘I’ve made a mistake’ but it is what it is, isn’t it?”
Over his time at Stamford Bridge, Hasselbaink scored 87 goals in 177 appearances for Chelsea and topped 20 league goals twice during his spell.
Kezman Move was a rare miss for Mourinho
Of the four forwards available to Chelsea that season, Mateja Kezman was meant to be a promising addition, but it didn’t take long for that decision to backfire.
In his only league campaign for the club, Kezman found the net just four times in 25 appearances before moving on to Atletico Madrid.
Having Hasselbaink available alongside Drogba and Gudjohnsen could have provided valuable depth up front, potentially helping Chelsea sustain stronger campaigns across multiple competitions.
The Blues may have finished top of the league table that season, but their cup runs were far less impressive. They crashed out of the FA Cup in the fifth round and exited the Champions League under controversial circumstances against Liverpool.
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