Arsène Wenger is in little doubt about where he places Milan on the podium of European superclubs. “Quite simply,” he mused, “they are the most consistent, the most effective and therefore the best European club of the past 20 years.”

Nor is this a piece of kidology after learning that Milan had on Friday been drawn with Arsenal for the knockout stage of the Champions League. Wenger had said it two weeks earlier when talking about Milan’s Kaka being awarded the Ballon d’Or. And he added, smiling: “That doesn’t mean they have to be the best for the next 20 years.”

You can measure the differences between Milan and Arsenal not just in decades but with whole generations. All great dynasties have their turning points and the Milan of five European Cups in 18 years, of seven Italian championships in the past 20, could cite all sorts of moments since the takeover of the club by a businessman with political ambitions called Silvio Berlusconi in the mid1980s.

Sometimes single results can be the genesis of gathering greatness, like, say, a 4-0 win against Juventus on the second Sunday of March 1989. The then Italian champions, featuring Franco Baresi and a trio of Dutchmen – Gullit, Van Basten and Rijkaard – wiped out Juve and later that spring would collect a first European Cup since the 1960s. Paolo Maldini was emerging as the finest full-back in the world, only 20 but in his fourth season in the team. Meanwhile, in London that weekend, Lynn Walcott was due. Little Theo came into the world four days later.

That is the moment everyone is primed for on February 20: when Walcott, England’s youngest ever international, ball at his feet, runs at the captain of Milan. The Arsenal player is 18, the Italian in his 40th year. One was born in the Swinging Sixties, the other at the tail-end of Thatcher-ism. It may mark the end of the great Milan dynasty, the one Wenger says need not go on for another 20 years. Wenger’s hope must be that this will be Maldini’s last European tie. The defender has announced that this, truly, will be his last season as a senior professional.

Maldini has waited a long time before he could even call himself the elder statesman of the Milan squad. Alessandro Costacurta only retired last summer, aged 41, after Milan had secured the Champions League at Liverpool’s expense. Maldini and Costacurta were not much older than some of their colleagues.

Milan were deemed to be close to their sell-by date when they beat Juventus on penalties as long ago as the 2003 Champions League final at Old Trafford with a side including Costacurta, Maldini and the Portuguese Rui Costa. When they met Liverpool in Turkey two years later, the same scrutiny was being applied to the band of thirtysomethings, Maldini, Costacurta, Cafu and goalkeeper Dida. By last May, when Milan reversed the defeat in Istanbul against the same opponents, the obligation had been to wonder if – besides Dida, Maldini and Alessandro Nesta – Clarence Seedorf, then in his 15th season as a senior professional, might still have the legs for it; to ask if Gennaro Gattuso could still snap and growl so fiercely in his 30th year, or whether Massimo Ambrosini’s unfussy game might have turned simply pedestrian in the week before his 30th. How much gallop would two 30-year-old full-backs, Massimo Oddo and Marek Jankulovski, have in them? And had not Filippo Inzaghi arrived back from injury by Tardis out of some distant galaxy? As it turned out, the final would be settled early in Milan’s favour, 33-year-old Inzaghi scoring both Milan goals.

All of those players are still at Milan, most have had another birthday since and it is plausible that coach Carlo Ancelotti’s lineup against Arsenal could include nine men aged 30 or over. Besides William Gallas, it is likely Wenger will select none who have passed that landmark. Age versus precociousness; or savvy against naivety: once the draw was known, Milan was echoing to reactions just like that of Arrigo Sacchi, the Milan coach of the 1980s and 90s.

“Arsenal are one of the best around,” he said, “but they lack experience.” But Milan currently lack their usual alibis against the suspicion that you can go on so long with the same, ageing core to a team. Their position in Serie A is dreadful by their standards with no excuses beyond a fixture backlog for having been at the world club championship earlier this month. Ancelotti’s team go into today’s derby against Internazionale trailing their neighbours, the Serie A champions and leaders, by 22 points, albeit with three games in hand.

Hence the louder cries for a big upheaval, some of those being shrieked by friends of Jose Mourinho, who might be a candidate should Berlusconi, Milan’s president, deem Ancelotti to be out of ideas. The coach has been in charge for six years, has just added the world club championship to two Champions League titles, one Serie A title and an Italian Cup with Milan, but a positive result against Inter would send him into the winter break feeling more comfortable about his position, and stronger in what he might recommend for retailoring his staff in January.

Andriy Shevchenko’s name cropped up again yesterday, raised by the club’s vice-president, Adriano Galliani. For all the evergreen qualities of Inzaghi, Milan miss a consistent centre-forward, which Shevchenko was at Milan before being sold to Chelsea. Kaka is their leading scorer in the league, just as he scored more than any Milan player in the 2006-07 Champions League. Last January Milan believed they had signed their new Shevchenko when they took Ronaldo from Real Madrid. But he has struggled for fitness and is unavailable for the Milan derby. Another Brazilian, the teenage Alexandre Pato, is eligible to play from next month and the hope, backed by his performances for Brazil’s underage teams, is that he may become as significant an addition as Kaka has been.

A day before Milan play in London, Inter take on Liverpool. The striking part of the DNA of the Italian champions is not their age but their cosmopolitan nature. The Inter lineup for the derby may well exclude any Italians, have a back four and goalkeeper all from South America,a midfield run by Argentinians, and the chief goal threat posed by the Swedish son of Balkan parents, Zlatan Ibrahimovic.

Ibrahimovic leads the goalscorers in this season’s Champions League and he and his Inter colleague Julio Cruz both have nine each from 16 Serie A matches. In support they have Hernan Crespo, the prolific Argentinian, and David Suazo, the Honduran.

Yet another centre-forward, the wayward Adriano, has just been sent back on loan to Brazil. Theirs is a squad about which Liverpool’s manager could play fantasy rotations long into the night. Not expected to start today, for instance, would be a long list of distinguished footballers: Patrick Vieira, Luis Figo, Marco Materazzi, Crespo, Suazo, Dejan Stankovic, Francesco Toldo, Olivier Dacourt. Inter held a seven-point lead over Roma in the table ahead of last night’s Roma-Sampdoria match and it sometimes is suggested that if Inter “B” took part in the championship it would be they, not the Romans, in second place.

But Italy in general feels that the alignment of the last 16 of the Champions League could hardly have been worse for their trio of surviving teams. Roma must face Real Madrid, and such is the Premier League’s recent history against clubs from Serie A that as much trepidation is felt in Lombardy as in London or Liverpool. Arsenal have been to Inter and Roma and won under Wenger, and they eliminated Juventus on the way to the final in 2006. Liverpool knocked out Juve the previous year and came back from 3-0 down against Milan in that season’s final. A decade ago, results between the two leagues would have showed a contrasting pattern. But Arsenal’s players would be too young to remember any of that.

Internazionale v AC Milan, today, C5, 1.30pm

Watching the clock: will Father Time take a toll on AC Milan veterans?

Arsenal’s tie with AC Milan pits Arsène Wenger’s young side against the European champions. Arsenal’s starting XI would probably feature only three players over the age of 26 whereas the Milan side, currently floundering in 11th place in Serie A, is likely to boast only one man under 28. Veteran striker Filippo Inzaghi is 34, while at 39, Paolo Maldini is the oldest player on either side

AC Milan (4-3-1-2)

Dida 34yrs 2mths
Oddo 31yrs 6mths
Nesta 31yrs 9mths
Maldini 39yrs 6mths
Jankulovski 30yrs 7mths
Seedorf 31yrs 8mths
Pirlo 28yrs 7mths
Gattuso 29yrs 11mths
Kaka 25yrs 8mths
Inzaghi 34yrs 4mths
Ronaldo 31yrs 3mths

Arsenal (4-4-2)

Almunia 30yrs 7mths
Sagna 24yrs 10mths
Toure 26yrs 9mths
Gallas 30yrs 4mths
Clichy 22yrs 5mths
Eboue 24yrs 6mths
Flamini 23yrs 9mths
Fabregas 20yrs 7mths
Rosicky 27yrs 2mths
Hleb 26yrs 7mths
Adebayor 23yrs 10mths

Average age Arsenal 25yrs 6mths Milan 31yrs 7mths

Italy gloom

Italy’s press wasn’t exactly bubbling with confidence after Friday’s draw. Gazzetta dello Sport grumbled: ‘We’ve done it this time. We’ve left the second-rate ties to everyone else. Milan [the city] versus England are two Champions League finals being played out early’

Corriere della Sera told Inter fans: ‘Remember Liverpool are only the fifth best team in England. They’re strong, but not super-strong.’ As for Arsenal? ‘They have French style and British heart, but we reckon it’s 52%-48% in Milan’s favour.’ Arrigo Sacchi, former Milan coach, was postively glum: ‘Terrible draw. Couldn’t be worse’