EXCLUSIVE
Rafael Benitez was the last manager of an English side to beat Real Madrid.
On February 25 in 2009 his Liverpool side won 1-0 at the Santiago Bernabeu thanks to a Yossi Benayoun goal. In the return leg at Anfield a fortnight later they thumped Juande Ramos's Madrid 4-0 to seal a resounding victory.
Here he gives his exclusive verdict to Sportsmail on whether Tottenham can follow in the footsteps of his Liverpool side.
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The main thing in Tottenham's favour tomorrow night is that they go to Madrid with nothing to lose.
They are big underdogs and they must not go to Madrid in trepidation but to embrace the occasion.
Winner: Yossi Benayoun heads home for Liverpool in the Bernabeu in 2009
The atmosphere and mental picture of facing Real Madrid can get to teams. They can be beaten in the mind before they even play - it is the same at Anfield.
At the Bernabeu there are 80,000 people pushing for their team, the fans may not be as close to the pitch as at Anfield, but they will be pushing strongly especially this year. This is a competition Real Madrid really want to win and you will feel that in the atmosphere.
However, I think Tottenham have enough players with experience of finals and the big occasion to handle it. It shouldn't be a shock to them.
For such a game as this, you have to be tactically prepared, of course, but you must be mentally strong.
It is one thing to say Tottenham are underdogs but that does not mean they go there expecting to lose. They have to have the right balance; relax but be sharp. Each player can not be too scared to say 'right I will play my game'.
When you approach these games it is no good thinking 'Oh Real Madrid can do that, so we need to do this'. If you get too involved thinking about the opposition you lose sight of your own style.
Heavy burden: Rafa Benitez belives a lot depends on the fitness of Gareth Bale
Tottenham need to play their own game. They have Gareth Bale, Rafael Van der Vaart and they have Peter Crouch who is good in the air. All influential players who give them two or three different options of attack. The ability to play to those strengths has got them this far in the competition and there is no need to change.
You can have a plan but you must be able to adapt. If the game changes you need to be able to move with it. So if they approached it with a rigid system to restrict Madrid it would more likely restrict them.
A lot depends on the fitness of Bale.
Madrid will play with a high line of defence to counter Crouch's ability in the air. They don't want him in the box using his height to set up chances but they know he lacks the pace to run behind them.
The key is in the wide areas. When Madrid go forward their full-backs, Marcelo and Sergio Ramos, like to push on to support the attack and that is where Tottenham can strike best. They must utilise the pace of Bale and Aaron Lennon to exploit the space behind Madrid's full-backs. I believe that and set-pieces will give them their best chance of a good result. Yet if Luka Modric can find the space to connect with Van der Vaart that can be dangerous too.
The trouble is I do not see too many weaknesses in Real Madrid's side. They have pace, they are good in the air. They have a lot of quality.
Comfortable win: Liverpool beat Madrid 5-0 on aggregate
As people know over here, Xabi Alonso can always find a pass, he can defend too, and going forward they have strong players such as Cristiano Ronaldo, Angel di Maria and Gonzalo Higuain who is coming back from injury.
Whether Tottenham have the defensive discipline to counter that is a question for Harry Redknapp.
The big difference since Liverpool beat Juande Ramos's Madrid is that they have spent big money.
Like Roman Abramovich did for Jose Mourinho at Chelsea, each year they have brought in very good players such as Alonso, Ronaldo, Benzema, Sami Khedira, Mesut Ozil and Di Maria. Florentino Perez has invested a lot into the team yet still Barcelona have been winning the trophies. Real Madrid expect to win a trophy every year. They have not won a trophy for two years and they need to win. They must win.
Everyone is pulling together now because they know how important that is but there is pressure with that. Maybe that could lead to frustration. It will be difficult for Tottenham but that pressure could give them their chance.
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?Explore more:People: Florentino Perez, Rafael Benitez, Cristiano Ronaldo, Mesut Ozil, Xabi Alonso, Peter Crouch, Harry Redknapp, Luka Modric, Sergio Ramos, Juande Ramos, Aaron Lennon, Gareth Bale, Jose Mourinho Places: Madrid, Barcelona, Liverpool
Source: Daily Mail
Source: Daily Mail