The 1998-99 season was a solid one for Leeds United, with the club qualifying for the UEFA Cup and finishing in fourth place in the Premier League – but a star player was about to leave.
Having only managed fifth place the season prior, Leeds clocked up eight more points and sat in fourth behind Manchester United, Arsenal and Chelsea. With Europe on the horizon, it was a good season.
It saw David O’Leary join in October, replacing George Graham and instantly the Irishman got the best out of the likes of Lee Bowyer, Harry Kewell and plenty of other players key to Leeds in the next few years.
But one player was more important than most. Jimmy Floyd Hasselbaink had joined Leeds for a bargain fee of just £2m in the summer of 1997. To many, Hasselbaink was a bit of an unknown when joining.

Jimmy Floyd Hasselbaink recalls being made a Leeds scapegoat
At this point, Hasselbaink had only played for a handful of small clubs in Europe – eventually leaving Portuguese side Boavista for Elland Road. Across the next two seasons, Hasselbaink starred in England.
He amassed 42 goals in his two seasons at Elland Road, 34 of which came in the Premier League and at the end of his second campaign, he entered contract talks with Leeds. But his demands were too high.
Talking to the Kammy & Ben podcast in 2022, Hasselbaink says he didn’t want to leave Leeds but when he requested a new deal, his terms were not met and was forced into handing in a transfer request by Leeds.
“I didn’t want to leave, I wanted to sign a new contract. I had two years left and I was in line to get a new contract, I was doing well. When I came, nobody knew me so my contract was that of an unknown player.
“They offered me a new contract but it wasn’t great. I wasn’t one of David O’Leary’s favourites. He took over and he wanted his own team. Chelsea came in for me, but they didn’t want to sell me to Chelsea.
“I told them the rate was for my contract and I wanted to sign, they said no. I said OK, then I want to go. They told me I’d have to hand in a transfer request, but you all know the hoo-hah that comes with that.
“I asked for the transfer request, and then they hung me out to dry. There was no way back. It didn’t have to go that way. I was well liked by the fans, and they needed a scapegoat, and the scapegoat I was.”
| Club | Years | Games | Goals | Honours |
| Telstar | Youth to 1991 | 4 | 0 | N/A |
| Alkmaar | 1991 to 1993 | 46 | 5 | N/A |
| Campomaiorense | 1995-96 season | 34 | 12 | N/A |
| Boavista | 1996-97 season | 38 | 24 | Portuguese Cup |
| Leeds | 1997 to 1999 | 87 | 42 | N/A |
| Atletico Madrid | 1999-2000 season | 43 | 33 | Copa Del Rey runner-up |
| Chelsea | 2000 to 2004 | 177 | 87 | FA Cup runner-up |
| Middlesbrough | 2004 to 2006 | 89 | 33 | UEFA Cup runner-up |
| Charlton | 2006-07 season | 29 | 4 | N/A |
| Cardiff | 2007-08 season | 44 | 9 | FA Cup runner-up |
| Total: | 581 | 249 |
What could have been as Hasselbaink went on to shine…
Sold to Atletico Madrid for a £12m fee, Hasselbaink went on to enjoy a stellar career in which he scored 33 goals in his only season with the Spanish side. He returned to England with Chelsea after prior interest.
Another 87 goals followed in just 177 games with the Blues before going on to shine with Boro. Leeds did boast the likes of Mark Viduka and Alan Smith over the next few years, but Hasselbaink was missed.
Had he remained at Elland Road and Leeds offered him better terms, the striker might have been the difference between remaining outside of the top three and breaking in – but ultimately, financial collapse.
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