The latest instalment of our Classic Calcio series takes us back to May 11, 2001 and a Friday night to forget for Inter Milan after they were humiliated 6-0 by their city rivals.

A lot of water has passed under the bridges of the Navigli since AC Milan and Inter Milan first crossed paths in 1909.

At last count, 243 matches had followed that historic first meeting. From title deciders to Champions League semis, Coppa Italia finals to clashes that delivered some of the most iconic pictures in the game, the Derby della Madonnina has seen it all.

And yet, even within such a rich and varied tapestry, nothing comes close to the events of May 11, 2001 when Milan vanquished their rivals 6-0.

It remains Inter’s biggest defeat in a derby. So comprehensive was the humiliation that even the late Milan owner Silvio Berlusconi, a man not exactly renowned for his decency and integrity, felt his side had gone too far.

“We should not have gone past 4-0,” he told La Gazzetta dello Sport in 2020. “I gave the players a dressing down. You shouldn’t humiliate the opposing team, it’s against the spirit of sport. It’s just not on.”

Berlusconi was conspicuous by his absence at the San Siro, missing the game to hold the final rally of his electoral campaign in Rome. The impending general election also meant the derby had to be rescheduled to a Friday night for the first, and so far, only time.

Milan’s supremo had cut an unusually peripheral figure throughout the season as, not for the first time, his political ambitions took precedence over football.

There was a revealing vignette about the extent of Berlusconi’s hands-off approach in the summer.

“Who is that guy with the No 9?” he asked, according to La Gazzetta dello Sport, as Milan players went through their warm-up ahead of a pre-season friendly.

“He is a new signing. We just bought him from Vicenza. He was the Serie B top-scorer last season,” came the reply.

To which Berlusconi reportedly snapped back: “And that’s why he plays with the No 9?”

The player in question was Gianni Comandini, who had fired Vicenza to promotion to Serie A the previous season on the back of 20 goals in 34 appearances before winning the Under-21 European Championship with Italy.

Berlusconi, however, was unimpressed with Milan’s new £13m signing. At 23, Comandini may have been the future of Italian football – admittedly he turned out not to be – but he lacked the pizzazz and stardust of Milan’s previous No 9.

How could the Rossoneri go from a Marco van Basten or a George Weah to an U21 international who had spent the previous two seasons in Cesena and Vicenza?

But if Berlusconi ignored who Comandini was in the summer, he and 75,000 others inside the San Siro swiftly became acquainted as he fired Milan into an early lead.

The game was barely two minutes old by the time Paolo Maldini intercepted a Matteo Ferrari pass just inside the Milan half, the loose ball falling kindly for Serginho, who motored past Luigi Di Biagio and Laurent Blanc.

The Brazilian then squared the ball for Comandini, who stood alone in the box, nothing but green grass around him where Inter defenders were supposed to be. He swept the ball past Sebastien Frey to open the scoring and his Serie A account for the Rossoneri, his only previous goal having come against Dynamo Zagreb in the Champions League preliminary round.

Comandini soon added a second, heading Serginho’s cross past Frey with 18 minutes played after again being afforded the freedom of the penalty box by Ferrari.

“These are the nights you dream about when you’re a kid,” he said in the press conference. “I had a good one.”

In Milan’s history, only Paolo Rossi had scored twice on his Derby della Madonnina debut.

Cult-hero status assured, Comandini’s adventure at the San Siro came to an end three months later when Milan offloaded him to Atalanta. That second goal against Inter was to be his last for the Rossoneri, perhaps justifying Berlusconi’s suggestion that he was simply not cut out for the job.

To give Comandini his dues, the criticism could have been applied to several players on both sides of the Milanese divide.

Two years removed from one of the most unexpected Scudetto in their history, Milan were a team in transition.

The starting XI against Inter comprised survivors of the glorious Fabio Capello era such as Maldini, Alessandro Costacurta and Sebastiano Rossi along with an Alberto Zaccheroni lieutenant in Thomas Helveg.

Like Comandini, Federico Giunti and Roque Junior had largely forgettable careers at Milan, while Andriy Shevchenko, Gennaro Gattuso, Kakhaber Kaladze and Serginho would form the core of Carlo Ancelotti’s all-conquering side over the next five seasons.

Leonardo and Zvonimir Boban were left on the bench with Oliver Bierhoff, another hero of the 1999 Scudetto and a scorer in the first derby of the season along with the Croat, out of the squad altogether.

If this was Milan’s spell in the wilderness, Inter were in the middle of their banter years, long before the term became ubiquitous in the football lexicon.

The side that won the UEFA Cup in 1998 had been dismantled and while Ronaldo remained, his powers were significantly diminished by the serious knee injury he suffered 12 months earlier just six minutes into his comeback.

The Brazilian was forced to miss the 2000-01 season, while Roberto Baggio was hastily sold to Brescia in the summer after falling out with Marcello Lippi.

It left world-record signing Christian Vieri as the only survivor of the trio that had captured the imagination of the Nerazzurri fans when it was assembled at the beginning of the previous campaign.

Here, Vieri started up-front alongside Alvaro Recoba, with Ferrari, Blanc and Dario Simic forming the three-man defence in front of Frey, with Javier Zanetti and Vratislav Gresko as wing-backs.

Inter’s midfield trio of Javier Farinos, Stephane Dalmat and Di Biagio spoke volumes for the Nerazzurri’s deep pockets and their chronic lack of a coherent approach.

Third in Serie A 1997 when they lost the UEFA Cup final to Schalke on penalties, Inter went one better the following season, lifting the European trophy but finishing second to Juventus in Serie A.

The Bianconeri retained the Scudetto in controversial circumstances, winning the title decider 1-0 only after Inter were denied a stonewall penalty in Turin.

That proved to be the high watermark of Luigi Simoni’s tenure, with Inter slumping to eighth the following season and churning through three managers, blazing a trail that would become well-trodden over the next five years.

Desperate to dethrone Juventus, Inter owner Massimo Moratti signed Vieri and lured Lippi to Milan.

It is impossible to overstate how seismic a move this was for Italian football. In just under five years with Juventus, Lippi won nine major trophies and turned them into the dominant force at home and abroad.

But far from being the missing piece of the jigsaw, the Tuscan proved as ill-suited to Inter as his expensively-assembled squad were to him. 

Inter finished fourth in Lippi’s first term and lost the Coppa Italia final to Lazio, but he departed just one game into his second season, with the Nerazzurri losing away to Reggina after being knocked out of the Champions League by Helsingborg in the preliminary round.

Fresh from steering Italy Under-21s to European glory, Marco Tardelli seemed an odd choice to take over from Lippi.

Inter were frustratingly inconsistent under the 1982 World Cup winner, failing to win two consecutive games in Serie A until the end of January and getting thrashed 6-1 on aggregate by Parma in the quarter-final of the Coppa Italia.

Worse still was to come in Europe, where the Beneamata relinquished a 3-1 lead away to Alaves to draw 3-3, before losing 2-0 at home in the second leg of the round of 16.

European football had been a bitter pill for Milan too, with Zaccheroni losing his job after a home draw against Deportivo La Coruna knocked them out of the Champions League in the second group stage.

The managerial change proved an inspired choice with club legend Cesare Maldini winning four and drawing two of his first six matches in charge.

All the same, Milan arrived at the derby fifth in Serie A with 44 points, ahead of Inter on goal difference, their lowest position for the second Derby della Madonnina of the season since the 1984-85 campaign.

If Maldini was ruthless by sitting Bierhoff in the stands and Leonardo and Boban on the bench, Tardelli, as Zanetti recalled in his autobiography, stubbornly returned to three-man defence he reluctantly ditched in favour of the players’ preferred 4-4-2 just weeks earlier.

The disastrous results were there for all to see.

Eight minutes into the second half, Giunti swung a free-kick in from the right, the ball evading both sets of players before skidding past Frey to make it 3-0.

Having barely laid a glove on Milan in the first half, Inter collected a number of half chances, with Blanc heading wide, Vieri forcing a smart save from Rossi and Recoba firing a free-kick over the crossbar.

It was too little and far too late, as the Rossoneri again sliced through them at will.

Shevchenko motored forward from midfield, holding off Zanetti before feeding Giunti, who sprayed the ball out wide to Serginho.

The Brazilian surged past Ferrari and crossed for Shevchenko, who headed in Milan’s fourth and then swept in the fifth with 68 minutes played. Even now, the goal is absurd in its simplicity. Serginho squared the ball to Maldini just inside Milan’s half and he fed Jose Mari who had dropped back into midfield.

A replacement for Comandini, the Spaniard laid the ball off to Kaladze and spun away from his marker, leaving the Georgian room to advance. At this point Kaladze simply ran in a straight line between Zanetti, Benoit Cauet and Blanc, before squaring the ball across the box where Shevchenko converted the easiest of tap-ins.

The Ukrainian then turned provider, releasing Serginho with a superb through ball that split Inter’s defence before the Brazilian capped an extraordinary performance by stabbing past Frey.

By then, Moratti had already left the San Siro, the humiliation proving too much for him.

“I still remember the lads crying in the dressing room at half-time after that 6-0 hammering,” the former Inter president recalled. “I went downstairs and some of them were properly sobbing, real tears pouring out. ‘This is unbelievable’ I thought, ‘they’re actually crying’. I just couldn’t get my head around it. They were really crying. I walked out of the stadium at 5-0.”

Tardelli’s verdict on his only derby as as Nerazzurri manager was far more succinct: “What happened tonight is an absolute disgrace.”

Despite the thrashing, Inter finished the season in fifth, two points ahead of their city rivals.

Two days on from the 6-0 triumph, meanwhile, Berlusconi secured a similarly emphatic victory as his centre-right coalition swept into power with 45.57% of the votes, with the Milan president elected as prime minister for a second time.