The making of Roberto Di Matteo

Chelsea's caretaker is blue through and through, so could Abramovich possibly end up giving him the job on a permanent basis? Sam Wallace asks those who know the Italian best...

Once today's game against Tottenham Hotspur is over, Roberto Di Matteo will scarcely have time to catch his breath before preparations begin for Tuesday night's Champions League quarter-final first leg away to Benfica. This is the job he always wanted but if he is still Chelsea manager come August it will have meant that Roman Abramovich has failed in his attempts to sign one of the biggest coaches in the world.

Starting today at home to Spurs, so begins 12 days that will shape Chelsea's season and the temporary reign of Di Matteo, taking in the game in Lisbon, the visit to Aston Villa a week today and the home leg against Benfica. The Independent has spoken to some of those who have known Di Matteo well during his career and asked the question whether he could save Chelsea's season and convince Abramovich to give him the job long-term.

What is for sure is that, for all the famous coaches appointed by Abramovich, Chelsea have never had a manager with a closer emotional connection to the club since arguably the days of David Webb in 1993, another short-term appointment. "Even when he [Di Matteo] was with us and the league table was tight," the MK Dons chairman Pete Winkelman recalled, "the first question he would ask about after our game was: 'How did Chelsea get on?"

Di Matteo's Chelsea story began in the summer of 1996 when the club's manager Glenn Hoddle succeeded Terry Venables with England, Ruud Gullit took over at Chelsea and then moved to sign a young midfielder at Lazio who had caught his eye. It took Gullit a while to track down Di Matteo, who was in Italy's Euro 96 squad (where the assistant manager was Carlo Ancelotti) but he said that he saw something in the player that was worth pursuing.

Gullit, who was at the Etihad Stadium this week to watch Chelsea's 2-1 defeat to Manchester City in his role as a Sky Sports pundit, still recalls that first conversation. "I tried to call him first but he was with the Italian national team so he couldn't talk and when finally I spoke to him we talked in German," Gullit told The Independent. "I speak German as well. But he spoke German like I had 'Johnny Sauerkraut' on the phone. I thought 'Who the hell is this? Is this the right guy?' He comes from Switzerland so he speaks perfect German. But it was a strange thing.

"He was a vital player for me. I saw in the national team that he was a holding midfielder but I thought that he had a little bit more than that. When I was manager he had the opportunity to go forward because I thought that Dennis Wise was for me the ideal holding player. He [Di Matteo] scored a lot of goals so he proved that he could do that also.

"I had seen him play a lot. He was a very serious guy. He takes his stuff seriously. He enjoys it in a way that is different ... it is very difficult to get a smile out of him but when you do it is worth it. It is really worth it. We got to know each other and went on holiday together. We were quite close. When he was at MK Dons and then at West Brom I also went to the training ground to see how he was doing."

By the time Di Matteo had given up on his playing career in February 2002, ended by the triple leg break in a Uefa Cup game against St Gallen 17 months earlier, he owned two restaurants in London. As part of his pay-off from the club he was given shares in Chelsea by the then chairman Ken Bates, the value of which was realised when Abramovich bought the club, and became its sole shareholder, in the summer of 2003.

Marcel Desailly, another one of the big-name foreign players who signed to the club two years after Di Matteo, said that it was always his former team-mate's intention to pursue a coaching career. "At the time he was playing, the interest was not there," Desailly told The Independent. "But after his career I worked with him in a business project and straight away he was telling me, 'This is not for me, I'm doing it for the moment but I want to be a coach'. I said: 'Are you sure, why are you going to lose your quality of life?' He said: 'This is really what I want to do'."

Unlike so many Italian managers who are schooled at Coverciano, the football management university outside Florence, Di Matteo did his coaching qualifications in England under the auspices of the Football Association. He says he has never felt completely Italian having been born to parents who emigrated to Switzerland from Pescara. But then neither does he regard himself as Swiss. His wife is English and two of his three children were born in London. "I consider myself a truly European person," he told The Independent in an interview in 2010.

It was not until 2008, six years after he had quit playing football, that Di Matteo secured his first chance to manage. He inherited Paul Ince's MK Dons team when Ince left for Blackburn Rovers. Winkelman, who gave him the job, said that it was the intensity of Di Matteo that impressed him. "He had been a high-profile player so he was one of those that you had to put a lot of effort in to meet with," Winkelman told The Independent. "I found he was an incredibly focused guy. I thought to myself, 'You know what? I'm going to give this guy the job'."

Under Di Matteo, MK Dons missed out by two points on one of the two automatic promotion places from League One and then lost to Scunthorpe on penalties in the play-offs. Winkelman says that the playing style Di Matteo put in place at the club continues to this day. "He had a very tight set-up with Eddie Newton and it was Eddie's job to help implement what Robbie wanted to do.

"He [Di Matteo] is a very focused individual. He is a hard worker. I believe that so much about success is about working hard enough. In life, there will always be people who will be prepared to work harder and for a manager it is a particularly difficult job."

It has not always been plain sailing for Di Matteo. Even before his career-ending injury, he fell out with Gianluca Vialli, the Chelsea manager, and having won promotion with West Bromwich Albion to the Premier League in May 2010 he found himself sacked the following February. Gullit said that it was never obvious that his former player would be a manager but that now he is in place at Stamford Bridge it is clear that he has an affinity with Chelsea.

Gullit said: "[When he was a player] I didn't see him, let's say, in front of the team. Yeah, I saw him talking but that's different. I don't know how he functions that way. But certainly with Eddie Newton he is doing well. He did well at his previous team. I was very happy that he got the chance to prove himself.

"I hope that he can continue with Chelsea because it is an important thing that he is from Chelsea, he knows Chelsea. The guys who are with him respect him for what he did for the club and therefore it feels home for him."

The prospect of Di Matteo getting the Chelsea job in the long-term was not unimaginable for Desailly either. Now a pundit, mainly on French television, Desailly played his final season for Chelsea in the first year of the club's new era under Abramovich.

"He [Di Matteo] was very English like. His was not really 'Latin' behaviour. He knew exactly what he wanted for his 'after' career and he wanted to be a coach. He is very low-profile and really accessible. I am sure as an assistant he has done a good job and as a main coach, if you give him the opportunity at Chelsea or somewhere else, he will perform. He will perform because he is not strict. He allowed room.

"This is difficult. To allow the room for mistakes, for players who don't respect the discipline, or the discipline of the tactical set-up. For me, he has the potential in the future to be a very, very good coach. He was very important in the Chelsea team. You were not asking him to make the difference. But tactically he was always available to fill the gap left by his team-mates."

A win over City would have sent Di Matteo into today's game against Spurs with five straight victories in all competitions in his short time as Chelsea manager and knowing that a win would lift his side above today's opponents into fourth place. Defeat has increased the pressure again. Lose today and if Newcastle United beat West Bromwich Albion tomorrow, Chelsea will slip to sixth place with eight games to play.

"What Robbie has had throughout his career has been that affinity with Chelsea," Winkelman said. "I don't think he will be overly concerned with the long-term. I think he is excited to have the opportunity with Chelsea with so many serious games coming up. If he does a good job and cements his relationship for the long-term – anything can happen at any moment. It's part of the excitement."