Pippo Inzaghi pouted, put on the anxious, eyebrows-slanted look of puzzled outrage to which his face naturally lends itself and wandered from the pitch at San Siro. He had just been substituted and, this being the stage of the season when players want to boost their goal tallies, he made clear what he thought of being replaced.

Inzaghi’s gesture set an agenda at the post-match press conference. What had Carlo Ancelotti, the man who took off Superpippo, made of the diva? “I am used to Pippo,” replied Ancelotti, cool and with the air of one who has seen it all before. “I know how he is, he knows how I am. He likes a bit of drama sometimes.”

Case closed, 35-year-old striker cut down to size. Ancelotti can be politely withering when prompted.

That was last Sunday, after Milan’s draw with Juventus, the first Serie A match in a run of six in which they had dropped points. Yet this has been a poor season for the club and coach with the pre-eminent record in the Champions League. Milan did not even participate in it in 2008-09 and for a while their presence there next time was in doubt. Hence the tension that has developed between the Milan president, Silvio Berlusconi, and Ancelotti, who is reaching the end of an excellent eight years in charge.

Ancelotti has won the Champions League twice in the past six years, a concentration of success matched only by Ottmar Hitzfeld and Vicente del Bosque, which is what has lately made him so attractive to the sorts of suitors whose principal target is achievement in Europe: Chelsea, Real Madrid and Bayern Munich. With his urbane manner and a pragmatic diplomacy in dealing with the caprices of a headstrong, vain boss, Ancelotti appeals to Florentino Perez, who wants to return as Madrid president; and to Roman Abramovich he looks a most suitable employee.

This is not to say Ancelotti is a yes-man, a meek manager. He has simply cultivated a way of dealing with the sort of president ready to claim, as Berlusconi once did, that he, and not the coach, designed the tactics and substitutions made during the Champions League triumph over Juventus at Old Trafford in 2003.

A firmer Ancelotti will meet the Milan management in the next 48 hours to learn whether they want him to stay for the last year of his current contract. There are strong grounds for believing the meeting will usher in the end of his Milan era.

Equally, there are those in Milan reluctant to see their “Carletto” join a European rival. The fear is that Ancelotti could do for Chelsea, their ageing squad and ambitious owner what he has done with Milan’s veterans. Analysis of the age of the current Chelsea squad can seem hysterically gloomy when you count up the birthdays accumulated by the second-best team in Serie A: Paolo Maldini is over 40 and Inzaghi, David Beckham, Giuseppe Favalli, Gianluca Zambrotta, Massimo Ambrosini and Rino Gattuso are well into their 30s.

The roll-call alone suggests how well Ancelotti has deployed those at his disposal. Milan were supposed to be growing too old when they won the Serie A title in 2004. They were deemed to be a team well beyond the optimum age to perform without symptoms of fatigue when they won the Champions League final in 2007. The 2009 version, granted, do play at a certain pace, but somewhere at Milanello, the club’s training ground, the coach has found a way to make senior, talented players into Peter Pans.

He has rejuvenated careers. Clarence Seedorf joined Milan from Internazionale in 2002, his progress having veered into a cul-de-sac. Ancelotti recovered the vim of Seedorf’s prodigious youth and Milan still benefit from the Dutchman’s intelligence. Andrea Pirlo was another who had lost his way at Inter. He joined Milan as an attacking midfield player until Ancelotti one day surprised Pirlo by telling him to remould his game at the base of midfield, an inspired idea.

Necessity breeds this sort of resourcefulness. Milan and Berlusconi have long had a weakness for the glamour transfer and Ancelotti has seldom dictated their signings. So he currently shuffles a squad with four or five men who would call themselves No 10s and finds ways of fielding Kaka, Ronaldinho, Seedorf and Pirlo in the same XI. Frequently he then has to listen to Berlusconi complaining he has lined up only one centre-forward, that he has an obligation to play football with panache. Mostly, his Milan teams have done.

This accommodating Ancelotti has had his failures, too. Followers of Chelsea will know him as the manager who could not find the right place in his Parma team of the late 1990s for Gianfranco Zola, who responded by moving to London. He is the manager in charge of two of the most vivid capitulations in recent Champions League history, when his Juventus lost a two-goal lead in Turin to Manchester United in the Champions League semi-final of 1999 and whose Milan were 3-0 up at half-time in the Istanbul final of 2005 and lost to Liverpool.

These setbacks are answered by the silverware he has gained. Should he move to England, he may need to remind sceptics of those successes. And that is not his style. His dealings with the media are unamplified and, where he works now, rather cosy.

He has given an impression during the heated wonderings on his future over the past month of being embarrassed. “It’s grotesque,” he said last week. “I feel like I’m on Big Brother.” Should he join the Premier League, he had better get used to it.

Managers who fell to earth

Silvio Berlusconi imagined many of the generation of footballers who took Milan to greatness in the late 1980s and 1990s would become great coaches. For a while, he seemed to be right.

Ruud Gullit made a dashing start as player-manager of Chelsea in the late 1990s. Frank Rijkaard was national coach of Holland by Euro 2000. Roberto Donadoni would soon enough be embarking on a career that would hoist him to the Italy hot-seat. Marco van Basten took the Dutch national job as his first senior coaching post.

But most have fallen to earth. Rijkaard had five eventful seasons as head coach of Barcelona but has been unemployed for a year. Donadoni’s stock fell at Euro 2008. Van Basten has just left Ajax, having failed in his first club job, and Gullit has flopped repeatedly since leaving Chelsea.