Chelsea must travel to Yorkshire for the quarter-final tie almost immediately after returning home from Japan following their Club World Cup final disappointment. With the Blues' recent form also having been indifferent, and interim manager Rafael Benitez battling to win over the fans, Hasselbaink believes Championship side Leeds can follow neighbours and Arsenal conquerors Bradford into the last four. Hasselbaink said:
"For Leeds, obviously, to be able to play in a quarter-final of the Capital One Cup is absolutely magnificent.
"They will have a good chance of going through to the semi-finals.
"They have seen Bradford doing it so I think they will take great inspiration from that and will be looking forward to the game. The game can't come quick enough for them.
"If I was Chelsea's manager, I would want to have a few more days to prepare for this match.
"They will have to go through it and hope they turn up and do not feel too tired. "The odds are getting better and better for Leeds."
Hasselbaink, 40, played for 10 clubs throughout his 18-year career but first made his mark in England with Leeds in the late 1990s. After a brief spell at Atletico Madrid, he joined Chelsea in a then club record £15million deal in 2000 and went on to score 88 goals over four seasons at Stamford Bridge. The side's attack is now led by £50million man Fernando Torres, whose form remains the subject of intense scrutiny. The 28-year-old has struggled to recreate the prolific form of his youth and a recent goal glut was undermined by a tortured display in the Club World Cup final loss to Corinthians. Hasselbaink believes the former Liverpool striker can still get back to his best. The Dutchman said:
"I don't know - but why not? He just needs to believe in himself more. "He is struggling a little bit with his confidence but that will only get better the more he scores.
"If he does, then I don't see why he couldn't get back to his Liverpool form.
"At least he is getting goals. He has got 12 so far.
"The only thing I can say is I would like to see him score more in 1-0s and 1-1s, those kind of goals. There are not enough deciders."
Given Chelsea's heavy schedule, Benitez may leave Torres and other senior stars out for the trip to Elland Road but Hasselbaink does not think it is a game the manager can afford to take lightly. Benitez was an unpopular choice to succeed sacked Champions League-winning boss Roberto di Matteo, who was a former team-mate of Hasselbaink. Hasselbaink, who is now first-team coach at Nottingham Forest, said: "They are out of the Champions League - they can't compete for that now. "And they will have wanted to win that game on Sunday and take that cup home. That was a big setback.
"He wouldn't want to lose the quarter-final in the Capital One Cup straight after.
"That would only bring more pressure and the more pressure he can relieve the better.
"All teams need to win games but I don't think it would do him big favours if he loses against Leeds."
As for Leeds, Hasselbaink has been saddened by their plight since their relegation from the top division in 2004. Following the recent announcement of a takeover, he expects them to return in the near future - although not at his current side's expense. He said:
"It is a pity to see the club where it is, it is a beautiful club that should be in the Premier League.
"Hopefully next year or the year after they can get back to the Premier League because that is where they belong.
"But I don't see them coming back this year because we are better.
"I am not saying that because I am at Nottingham Forest, I am just saying that for football reasons."
Leeds and Chelsea have a fierce rivalry dating back to their clash in the 1970 FA Cup final. Hasselbaink knows that has not waned and even expects extra edge given Leeds chairman Ken Bates' previous guise as long-running Chelsea supremo. He said:
"I think it will still be there, and maybe a little bit more with Ken Bates against Roman Abramovich.
"I think the Leeds supporters will relish this game and be looking forward to it."