Up in the VIP seats at San Siro, Paolo Maldini and Javier Zanetti will itch to be taking part. Maldini, now 54, played in eight European Cup semi-finals at the city of Milan’s great, shared sporting theatre.
Since retiring, he has spent long years wondering if the club of his lifetime, the AC Milan where he is now a director, might ever keep such elevated company again.
Zanetti, 49 and a vice-president of Inter Milan, spent much of the last decade nursing the same fears for the club he served as a player for 19 seasons. In his time, he played in two San Siro Champions League semis and lifted the trophy on the last occasion any Italian team were Europe’s club champions.
Twenty years ago this week, they played their highest stakes derby, Zanetti and Maldini opposing skippers on the only previous nights the reds and blues vied over two legs for a place in a European Cup final. But if they are the highest-profile link between Wednesday’s all-Milanese semi-final and a distant era of superpowered Italian football, there will be many others on site relishing the sequel.
Seated in the grandstands, regretting the injury that caused him to be left out of Milan’s Uefa-registered squad will be Zlatan Ibrahimovic, still, at 41, a Milan player. Back in 2003, he was an ambitious Ajax striker, on the losing side to Maldini’s Milan in the quarter-finals and on the cusp of a move to Serie A, where he accumulated trophies with Inter and Milan.
Much closer to the action will be Federico Dimarco, the dynamic Inter left-back who has a faint memory of watching the 2003 "Euroderby", won by Milan on away goals, as a five-year old Inter fan.
Another interested observer then was Simone Inzaghi, the manager who has now taken Inter further in Europe’s principal club competition than anybody since Jose Mourinho guided Zanetti and colleagues to a Treble in 2010.
Inzaghi will forever be a resonant surname around San Siro: Simone’s older brother Pippo was an AC Milan striker whose poached goals galvanised two triumphant Champions League runs and who scored twice in the 2007 final against Liverpool. That marked the last of Milan’s seven European Cups, the fifth of Maldini’s evergreen career as a high-class defender.
If history weighs heavily on Wednesday night – as do vividly remembered tensions around the 2005 Champions League quarter-final derby, abandoned during its second leg because of flares thrown from the stands – Italian football looks on this, a guarantee of Serie A having a Champions League finalist for the first time in six seasons, as a sign of rejuvenation.
The league has novel champions, Napoli having last week sealed their first scudetto since 1990; Milan, Serie A winners in 2022, and Inter (in 2021) both ended 11-year waits to claim those titles. There is a prospect of Roma, Juventus and Fiorentina further showing off the league’s strength in depth in Thursday's semi-finals of the Europa and Europa Conference Leagues.
Maldini can take personal pride in Milan’s recent rise. Under his watch, younger talent has been brought in and developed alongside carefully selected veterans such as Olivier Giroud and, when fit, Ibrahimovic.
The defence that has conceded no goals through very nearly six successive European games – until Napoli scuffled an injury-time strike past totemic goalkeeper Mike Maignan last month – puts trust in 22-year-old Pierre Kalulu and the 25-year-olds Fikayo Tomori and Theo Hernandez. Two 23-year-olds, Stefano Tonali and Brahim Diaz, have shone in midfield.
The chief concern for Milan manager Stefano Piolo ahead of the first leg is the fitness of Rafael Leao, 23 and their most potent and creative forward, who picked up a muscle injury at the weekend and trained apart from teammates on Tuesday. “I’ll make a decision on him based on what I hear from the medical staff and Rafael,” said Pioli.
“We know Leao’s importance,” Inzaghi responded, “and we may make small adjustments if he’s in or out, but our game plan won’t be disrupted.”
In Inzaghi’s rear-view mirror is Leao’s match-winning performance in the 3-2 derby win early this season. Fresher in his mind are the last two derbies, a 1-0 Inter victory in the league in February and a 3-0 Inter triumph in January’s Italian Super Cup in Riyadh.
“We've played seven derbies in the last 20 months, won some and lost some,” said Inzaghi. “In the latest ones we had clarity, unity and covered every inch of the pitch. We'll have to be good in every phase of the game.”
