Jimmy Floyd Hasselbaink: 'Nobody expected us to go this far, not even ourselves'

Two years ago Jimmy Floyd Hasselbaink sat on a pitch in Eindhoven and, in his own words, "shed a single tear". Middlesbrough had just been beaten in the Uefa Cup final by Seville – and beaten rather badly. No one carried the pain of the 4-0 humbling any more personally than the Dutchman.

"I could only feel what might have been," he said. "It was very sad for all of us to end the season like that and fly back to England without the trophy. And for me I was thinking that perhaps this was my last chance of glory."

It wasn't. Hasselbaink has one final shot at the career-defining medal that has bafflingly always eluded him at Wembley this afternoon, and if it is possible that eyes can say anything at all, then those gleaming balls of intent that shone throughout this interview fairly screamed that this will be his moment. And Cardiff City's, too, of course.

"Listen, if you had said that we were going to go to the FA Cup final this year I would have punched you," said Hasselbaink. "I'm serious. I would have. The very least I would have done was say something nasty to you – 'Don't take the piss', or whatever. Nobody expected us to go this far, not even ourselves. I thought my only FA Cup chance was the one I had in 2002. It's just great. I'm sorry, I don't have the exact words for it."

No matter, "just great" happens to sum it up nicely for a 36-year-old who came so close to quitting at the end of last season when Charlton were relegated and the Premier League turned its back on one of its most prolific scorers. Hasselbaink had always vowed not to drop through the divisions. "I will not play at a lower level," he promised in his 2005 autobiography, Jimmy. "I only want to play in the Premier League and if possible Europe." So this was it, as his agent informed him that the mobile had remained silent. Decision time. "Yeah, I did consider it," admitted Hasselbaink. "And I did almost retire. But the people around me and who know me best convinced me not to. I thought, 'OK, let me play for another year or two'. Why not?"

More than one or two of the Cardiff faithful would undoubtedly have told him why as he struggled to adjust to life in the Championship. To the uninitiated – dare it be suggested ignorant? –football observer, Hasselbaink never has done a great deal except score and as he stood there, with his back towards goal, the ball at his feet and as the clock ran by and the chances seemingly went begging, the cruel word on Ninian Park's Bob Bank was that they had witnessed vasectomies reversing themselves quicker.

Hasselbaink now acknowledges that the downgrading was not at all comfortable. "I've had a few bad matches, but the Championship is not that easy," he said. "I've played for some big clubs on the big stage and playing in the Championship is a lot different because everything goes a lot quicker. Don't get me wrong when I say 'quicker', it's just a lot more direct. In the Premiership you have two passes, three passes and then you start an attack or whatever, but in the Championship it's quite like back in the day when I first signed for Leeds. The Premier League has changed so much. It's more continental now. And changing from that was my biggest test. Actually, I would have thought I would have scored a lot more goals, but the manager has asked me to do other things for the team. Basically using my experience at certain times."

Dave Jones has indeed played it cannily with Hasselbaink and seemingly still is, by not offering him the one-year extension on his contract until after this final. Hasselbaink is adamant that he is not retiring "win or lose on Saturday" and feels he will still be at Cardiff next year. The hints are encouraging as Jones has acknowledged that the old boy has become an invaluable figure around the training ground. Both to raise the heat and, yes, to intensify it. "Yeah, I've fallen out with Jimmy Floyd at stages this season," confessed the centre-half Roger Johnson the other day. "But then, you tell me who hasn't fallen out with Jimmy Floyd."

At Cardiff, no one. Or no one that is, who is not a youngster who would hesitate saying boo to a goose, never mind to a fully fledged Premier League legend. "I love it," said Hasselbaink. "It's the kid coming out in me and the day I don't care any more, that's the day I'm going to stop. I want to train every day and, yes, I'm one of the biggest moaners there. But I love having that confrontation with players like Roger [Johnson] and Glenn [Loovens] because they don't have a clue! No!

"Seriously, on the training pitch there is no respect and I like that. I don't mind him kicking me and he doesn't mind me kicking him back. That's how it has to be. But when we come off there has to be respect for each other. That's the beauty of it and that's the beauty of our squad. We have great camaraderie."

Never was this more evident than at the Christmas bash in Ireland. At the time, the club was in a state of utter turmoil as a series of bad results on the pitch had been rendered pretty irrelevant by a court battle off it, that at one stage looked odds-on to haul Cardiff into administration. Jones was, allegedly, on the brink of losing his job (The Times and The Guardian even had him "sacked" one particular morning") and the squad was inevitably to break up. So what did they do? They did what Frank Gallagher always advises on Shameless, a favourite programme of Hasselbaink's. They had a party. And became tight. Ever so tight.

"Everybody had to wear a costume and do you know what I wore?" he laughed. "A fucking kilt! And a 'see-you-Jimmy' wig. Well my name is Jimmy. Aye. Everything was done properly. I had my knife in my sock. And under my kilt? I said I did it properly. Totally! Someone asked me what I'll dress up as at the party if we win the Cup. 'Whatever you want, mate!' I told him. 'Whatever you bloody want.'"

Hasselbaink's mind trailed away as he thought of what could be. "I'm excited, yes as excited as the kids, as excited as Aaron Ramsey [Cardiff's 17-year-old]. He doesn't show it, but he is. Just like me. It's more inside, and I think come Saturday, 5pm, it will all burst out. It's just crazy. But if you look how we got there, it's also deserved. Yeah, we had a little bit of luck with the draw, but then so did Portsmouth. They did go up to Manchester United and win, but [other than that] they played Championship clubs. We genuinely believe we can win. We are certainly good enough to."

It is a conviction born out of a run in which the Championship mid-tablers unarguably played their best football of the campaign. In many respects the Cup has saved Cardiff's season, just as it has made that of Hasselbaink. Certainly, among a critical support his place was cemented by a fifth-round strike against Wolves that rivalled his very best when topping the Premier League scoring charts in 1999 and 2001. "It was a beautiful goal, a beautiful moment," he said with trademark modesty. "But now that is gone." What is left is the chance to add to his paltry silverware collection of one Portuguese Cup medal. Not quite Ryan Giggs, is it, Jimmy?

"Yes, that was my first cup final [in 1997 with Boavista] and it is the only one I won," he said. "But, in all honesty, I don't think it is possible to compare the Portuguese Cup with the FA Cup. The FA Cup is 10 million times bigger. Everybody watches it over the whole world. It's amazing. Every little boy who wants to be a footballer wants to win the FA Cup, wherever he is growing up. Why? I don't know. I think it is partly Wembley, and partly because everybody can beat everybody in the Cup. It is just the history of it that makes it a little bit more special.

"And this time that probably applies more than ever. We haven't had a year like this for some time, what with a Championship club going there with a real chance. Yeah, you had Millwall a few years ago, and they did fantastically well to get there. But they played Man United and everybody knew that United were going to win easily. To be fair, yes, Portsmouth are the favourites. But nobody knows who is going to win. And that's the wonder of it. That's the wonder of football."

Hasselbaink can say so from a position of some privilege. As a youth in a rundown suburb of Amsterdam, Hasselbaink spent time in a detention facility and was a tooled-up member of a notorious gang. Football provided his escape and grateful does not begin to describe the way he feels towards his profession. Still, the bad memories do come flooding back on occasion and when he looks at local lads such as Ramsey and the equally precocious Joe Ledley at around 2.45pm today he could be forgiven for shaking his head. Will they ever realise how fortunate they are?

"Like I said that's the wonder of football, the beauty of Wembley if you like," he said. "Some players have the chance to be able to get there when there are 17 and some players never get there at all. And then what happens when they do get there? Some like Giggs have been there six, seven, eight times and been on the winning team very often. But players like Giggs are the exception. The ones who never get there, now they are the norm. Yes, those boys in our dressing room are lucky."

Hasselbaink is determined to prove just how lucky. Before running out, he will bark encouragements in their ear and surely remind them of all the times he has had the better of Sol Campbell and Sylvain Distin – and conveniently forget all the times he failed to. "But I won't give them advice or anything," stressed Hasselbaink. "When you go in and talk too much to them they are going to get nervous. You just need to pat them on the back, and say, 'Go out and play. Go do your thing.' I'll certainly be doing mine."

Loss leader: Hasselbaink's near misses

*1998 World Cup semi-final. Lost. Brazil 1-1 Netherlands (Brazil won 4-2 on pens)

Although Hasselbaink didn't feature on the night, he had played in the group stages and was very much part of the Dutch squad who came within a penalty shoot-out of a World Cup final. Misses from Phillip Cocu and Ronald de Boer sent Brazil through.

*2000 Copa Del Rey final. Lost. Espanyol 2-1 Atletico Madrid

Hasselbaink's first major final was in Spain at the age of 28. Unfortunately for him, Atletico were on terrible form, relegated, and folded to a 2-1 defeat that could have been worse.

*2000 Relegation from La Liga. Atletico Madrid

In Hasselbaink's only season in Spain Atletico were relegated. Despite Hasselbaink scoring 24 goals in 34 league outings Atletico finished seven points from safety.

*2002 FA Cup final. Lost. Arsenal 2-0 Chelsea

Second-half goals from Ray Parlour and Freddie Ljungberg lead Arsenal to victory in Hasselbaink's first and only English Cup final until this year.

*2006 Uefa Cup final. Lost. Seville 4-0 Middlesbrough

Seville battered Middlesbrough from start to finish in what was the biggest single-leg Uefa Cup final victory. Mark Viduka saw Boro's best chance saved and goals from Luis Fabiano, Enzo Maresca and Freddie Kanouté left Hasselbaink and Middlesbrough with losers' medals.