Chelsea eye AC Milan mark as they open case for Champions League defence against Juventus

Chelsea begin the hardest challenge in football tonight. Winning the Champions League is tough enough. Retaining the most prestigious trophy in the game, though, is something else – and another feat Roberto Di Matteo is determined to accomplish.

During the Champions League era no team has won the trophy in consecutive years. It was last successfully retained as the old European Cup, when the Milan side featuring Marco van Basten, Franco Baresi and Ruud Gullit won it in 1989 and 1990.

Better teams than Di Matteo's, it must be said, have tried and failed. Pep Guardiola's Barcelona were blocked out in the semi-finals in both 2010 and 2012. In the Champions League era only four holders have ever even reached the final next time and lost: Milan in 1995, Ajax in 1996, Juventus in 1997 and Manchester United in 2009.

But who would have predicted six or 12 months ago that Stamford Bridge would be adorned tonight with the livery of European champions? Not many when they lost 3-1 in Naples in February, precipitating Andre Villas-Boas's departure as manager. Not many when John Terry was sent off in the Nou Camp, or when Andres Iniesta put Barcelona 2-1 ahead. "It has just proven so far to everybody impossible to win it twice," said Di Matteo last night. "It will be difficult, for sure, but we will try, try to do the impossible."

For eight years Chelsea had been striving to be European champions. Now they are, Di Matteo knows the focus needs to move on. "There's always new challenges every season, a club like Chelsea will always try to win trophies and be successful," he said. "It's not looking back at what you achieved, that's done and dusted."

Having upset more accomplished teams in Napoli, Benfica, Barcelona and Bayern Munich last year, Di Matteo knows that Chelsea are now on a pedestal and the constantly improving quality in the tournament will make his season very difficult. "I think [the difficulty of retaining] is because of the fierce competition that there is the Champions League," he said. "Every season gets new strong teams coming in like PSG and Juventus and so on. That makes it very, very difficult. Our players, they've got experience and confidence. I think every team now will face us with a little bit extra motivation because they're playing against the title holders."

John Obi Mikel knows the atmosphere is slightly different this season. "It does add pressure to us but at the same time we are more relaxed," he said. "We've done it. This club has done it now. But we don't want to relax. We want to build on what we did last season."

And yet Juventus have two European Cups of their own, as well as 28 domestic titles, and Di Matteo acknowledged their challenge. "They are a very strong team, everybody recognises that," he said. "They have quality, experience, some dynamic players. They are probably one of the most difficult teams you could be drawn against."

Last week he identified Pierluigi Casiraghi, Alessandro Del Piero and Angelo Peruzzi as three of the few players he knew who had mental strength comparable to that of John Terry.

He knows that even with Antonio Conte, another member of their Champions League-winning side of 1996, suspended as coach, they will bear his mark on the pitch. "I expect a Juve who want to play their game," he predicted. "That is the Conte way. They like to get on the ball and attack but we will try to eliminate the spaces on the pitch and fight back."

Orchestrating it all is Andrea Pirlo, a genuine giant of the game and a man who helped to bring Juventus the Serie A title last season. "He is an extremely talented player, which since his switch to Juventus he has shown again," Di Matteo said. "But it is not just him."

Kick-off 7.45pm, Stamford Bridge

TV Sky Sports 2.

Referee P Proenca (Port)

Odds Chelsea 6-5 Draw 11-5 Juventus 13-5