The Italian boss has it all to do again this coming campaign as he tries to repeat last season's remarkable silverware haul and deliver a more exciting brand of soccer.
Chelsea manager Roberto Di Matteo helped mastermind the most unlikely of doubles last season but unless he is able to accomplish the equally demanding twin accomplishments of adding style to substance this season, there is no guarantee he will last the campaign, according to his former Chelsea teammate Franck Leboeuf.
It is little more than three months on since Di Matteo staked an irrepressible claim to be handed the Stamford Bridge managerial reins on a permanent basis by delivering Roman Abramovich’s Champions League grail.
A raft of exciting new signings have arrived over the course of a hectic summer period which has served to heighten expectations, and Leboeuf, who spent six seasons at Chelsea, fears that barmy night in Munich is no guarantee of the much needed managerial stability the west London giant has lacked since Abramovich’s arrival.
"Of course not,” Lebouef told Goal.com when asked if he would be surprised were Di Matteo to be ousted before the end of upcoming season. “That's the main problem over the past 10 years - this switch from coach to coach and I think in football you have to try to have some continuity and that's been the main problem.
"Coaches haven't had the time to settle down and prepare something because, when you are Chelsea, you need results immediately or you're going to feel the pressure from the fans and from the media and you're going to chase that. If Arsene Wenger had been at Chelsea last season, he would have been sacked, while Andre Villas-Boas was."
With the club having already rifled through seven managers in just eight years since the famously trigger-happy Russian oligarch's takeover back in 2003, the onus has now changed and the goalposts have been moved - winning alone is no longer enough to sate the appetite of the baying masses on the terraces and the glutinous mouths in the boardroom.
Given the heavy investment during the close season in a number of burgeoning, creative talents, beautiful soccer is once again the order of the hour.
Of course, the term 'sexy football' was first coined by former player-manager Ruud Gullit back in the mid-90s when he managed a Chelsea team which included the playing talents of both Di Matteo and Leboeuf, and the Frenchman believes that it is about time the club returned to its pre-Abramovich roots in the pursuit of further glory.
"’Functional’ is a nice word [to use about Chelsea last season],” the France World Cup winner added. “I would say they were boring, that's what it was.
"I like football, I like good football and I like to enjoy football, but you need to entertain the people. It's not only about getting results and scoring lots of goals but entertaining the people.
"Chelsea was named a decade ago, maybe a bit more than that, the 'sexy' football team, so they have to go back to that while they keep on winning, which is a very tricky situation.
"We know that Di Matteo has an Italian background and an Italian footballing education, meaning that you first make sure that you are strong defensively to secure a result, then you know that you will have chances to score.
"They've bought the players for that, players that will bring pace to the game, we will see them playing very fast and they want to sustain that - I think Oscar, Marin and Hazard can bring that."
Having spent upwards of 65m pounds this summer on the aforementioned trio of Eden Hazard, Marko Marin and Oscar, the elegant former center back believes that the current Chelsea squad is good enough to mount a title challenge, despite the fact that the club finished a full 25 points off the summit last term and way back in sixth-place.
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He said: "Chelsea are the current Champions League holders and they will have to show in the Premier League that they're still there. Last season for them domestically, even though they won the FA Cup, was not good and they have to claw back that situation in the league.
"I think that the club are beginning a new cycle, new people, new players and you want to see if it works between them. But at Chelsea you need to win something and you can't really have another season like you did last year, to be that many points in the league behind both Manchester clubs, so you have to stick on in there and make sure that you start the season well."
There is no getting away from just how far in front both Manchester United and Manchester City were last season, though, and in terms of who goes into the new campaign as the outright favorite, while a challenge from west London may be required to keep Di Matteo in a job, Leboeuf believes Roberto Mancini's side still looks like the team to beat in what has been a summer of upheaval for nearly every other major club aside from the current champion.
"I see Manchester City being better than anybody else,” he said. “Mancini is complaining about not having new players but with the players he already has, he has a very good team. They know each other and I think they're going to be better than last season.
"With Manchester United signing Van Persie a few days before the beginning of the new season, Chelsea, Liverpool, Tottenham and Arsenal all having to adapt to new players, coaches and systems, this makes Manchester City the favorites. They know how to play, they know Mancini, there are no surprises and they are going to be better so they are a real threat."
While an exciting season is on the cards back home in England, casting his eye further across Europe, Stamford Bridge is not the only place welcoming the dawning of a new era, according to Leboeuf.
The main criticism often leveled at billionaire owners of clubs, like Abramovich, is that they are often accused of not being in it for the long haul, but the reinvestment in the squad this summer has bucked the trend in that respect, which brings its own pressures.
"We thought Abramovich would lose interest after the Champions League win but he bought new players into the club and showed his commitment to the club and it's a long-term vision - he wants to see the club winning the Premier League again and it's a good season to do so," stated Leboeuf.
You suspect that with just as many questions as he answers to address going into what represents a career-defining campaign for the 42-year old boss from Schaffhausen, that he must hope that this vision in question does not have an expiry date on it, or a revolving-door policy at its heart.
With so many balls up in the air with concerns to the club's new direction and the clear shift in focus to a more aesthetically pleasing style of play, it could take a blast from the past to inspire the new generation.
One thing is for certain, though, Di Matteo will have his hands full trying to not only meet expectations, but in adding the much sought-after glitz to an already glossy outfit. While comfort can be found in the history books, the club's own checkered past on the managerial front is another issue entirely.
Frank Leboeuf features on ESPN’s soccer debate show, ‘ESPN FC Press Pass’ and was speaking ahead of ESPN’s live coverage of the Barclays Premier League this season. For details visit: www.espn.co.uk/tv
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