The Greatest - Football Teams: Milan 1987-1994

The Immortals in 1990. The Invincibles in 1992. So good were Milan between 1988-1994, they named them twice.

Football is cyclical by its nature, and few clubs will understand that as well as Associazione Calcio Milan. The best post-war side in Italy, Milan were the team throughout the 50s, becoming the first Italian side to win the European Cup in 1963, before being cast adrift throughout the 70s.

But more than a decade after their last title, 1979 would see Milan crowned Italian champions for a 10th time.

Less than 12 months later, however, they’d be relegated to Serie B following the Totonero match-fixing scandal.

It was the first time Milan had been relegated from Serie A, and the reasons behind it made it the greatest of ignominies. 

Milan would keep much of the side together, including a 20-year-old Franco Baresi, already being labelled the new Franz Beckenbauer, while adding a 20-year-old Mauro Tassotti, as the back line that would take Milan not just back to Serie A, but the summit of Italian and European football, began to take shape.

Milan would bounce back at the first time of asking, only to be relegated upon their return to the Italian top flight, with the club’s poor financial situation rendering them unable to attract players of a sufficient calibre.

The Rossoneri would win Serie B once again, and re-establish a firm foothold in Serie A, finishing sixth in 1984.

The 84/85 campaign would see the introduction of a certain Paolo Maldini, who made his debut off the bench in January, and while Milan weren’t in a position to challenge for the title, they did qualify for European football once again whilst reaching the Coppa Italia final. 

After a turbulent start to the 1980s, by the middle of the decade, it seemed Milan were back on track. The departure of Nils Liedholm following the title win in 1979 saw Milan go through Massimo Giacomini, Luigi Radice, Italo Galbiati and Ilario Castagner before going back to Liedholm in 1984.

But the club was in financial turmoil. Fees for players were outstanding, as were wages to the players themselves. 

The saying that 'it’s always darkest before the dawn' rang especially true for Milan; the lights could quite literally have been turned out at the San Siro such was their perilous financial position, prompting the sale of the club to Silvio Berlusconi in February 1986.

TV tycoon Berlusconi sensed an opportunity with the new Serie A TV deal which would revolutionise Italian football, providing a cash injection into the league, attracting the biggest stars in world football.

By the mid-80s, Diego Maradona, Michel Platini, Zbigniew Boniek, Karl-Heinz Rummenigge, Socrates, Zico and Falcao were all plying their trade in Serie A, with Lothar Matthaus, Ian Rush, Rudi Voller, Jurgen Klinsmann, as well as Milan trio Ruud Gullit, Marco van Basten and Frank Rijkaard all following, and that was on top of the litany of Italian talent already there.

After five tumultuous years, Milan were again back in a position to compete. 

But a run of one draw and three losses which left Milan cut adrift in the title race saw Berlusconi, little more than a year into his tenure, sack Liedholm, with Fabio Capello taking temporary charge.

The next permanent managerial appointment would be one of the biggest landmark moments in the history of Milan – again, not that the fans could know that at the time.

Berlusconi made the bizarre decision to appoint Arrigo Sacchi in the summer. Sacchi was a relative unknown at the time, with fate playing a significant part in his appointment. 

Managing Parma in the second tier, Sacchi deployed a brand of football offering a breath of fresh air compared to the defence-first approach seen throughout Italy at the time. Not only entertaining, it was effective too, as Parma twice beat Milan in the Coppa Italia.

The Milanese media cast a deeply sceptical glance at Sacchi and the fact he’d never made it beyond the amateur ranks of football, prompting one of his most famous quotes, pointing out that you don’t need to have been a great player to be a great coach:

“Per essere un fantino non occorre essere stati un cavallo” – To be a jockey you don’t have to have been a horse.

Sacchi would get his big break in Lombardy, and would be supported with the financial backing of Berlusconi. 

The 1987/88 season saw three-quarters of their legendary back four play together for a third consecutive season, with Alessandro Costacurta making his Serie A debut in October. 

Meanwhile, Marco van Basten and Ruud Gullit arrived, a year before the legendary Dutch team were successful at Euro 88, as did Serie A winner, four-time Coppa Italia winner and European Cup runner-up Carlo Ancelotti. 

Milan weren’t just signing top players, they were signing the top players; Gullit won the Ballon d’Or a few months after signing for Milan while Van Basten finished sixth, himself winning it the following year.

Suddenly, after the struggles of the first half of the decade, Milan had star quality all over the pitch.

Regrettably, Marco van Basten would miss much of the season with an ankle injury that would ultimately cut his career cruelly short, but thanks to an incredible rear-guard that conceded just 14 goals in 30 games, Milan were champions again, ousting the previous season’s victors – Diego Maradona’s Napoli. 

With Paolo Maldini, Alessandro Costacurta and Franco Baresi at the back, and Roberto Donadoni in midfield, Milan had four players who’d earn a combined 329 caps for Italy, and they were already bolstered by Dutch greats Marco van Basten and Ruud Gullit before being accompanied by Frank Rijkaard ahead of the 1988/89 season, which would see them look to defend their title, and take on Europe…

The late 80s were a perfect storm for Milan and Italian clubs in general. After the new TV deal which sparked Berlusconi’s decision to buy Milan, Serie A clubs had the money to attract marquee foreign stars, even when rules only permitted two (and later three) non-Italian players per club. 

After the decade of English dominance, the ban of English clubs from Europe left a gaping void which the Italian clubs plugged. For seven years from 1989, Italian clubs had: 

• Seven European Cup/Champions League finalists and four winners;
• Four Cup Winners’ Cup finalists and two winners;
• Ten UEFA Cup finalists and six winners.

1988 saw Milan conquer Italy; 1989 would see them conquer Europe.

Adding Rijkaard to their ranks meant that Milan had 1988’s top three in the Ballon d’Or voting in Van Basten, Gullit and new signing Rijkaard.

On top of that, the would-be-legendary back four of Tassotti-Baresi-Costacurta-Maldini was complete.

Rivals Inter would march to the title, led by German greats Lothar Matthaus and Andreas Brehme, signed the previous summer, but it was in Europe where Milan would stamp their legacy on the game.

They required penalties to get past 1991 European champions Red Star Belgrade before beating Werder Bremen 1-0 on aggregate. The 1-1 draw in Madrid against European giants left the second leg in Lombardy finely poised.

The tie would be finely poised for no more than half an hour, by which point Milan had raced into a 2-0 lead, making it 3-0 before half-time, with Van Basten and Donadoni completing the rout inside the hour. 

European giants Real Madrid hadn’t just been beaten, they’d been pulverised into submission.

And though it was a Madrid side that hadn’t won the European Cup since 1966, they’d won the UEFA Cup in 1985 and 1986, before reaching a third straight European Cup semi-final when meeting Milan. 

They’d also win the league and cup double at home – their fifth consecutive league title. Spearheaded by the great Hugo Sanchez with Bernd Schuster in midfield as well as the Quinta del Buitre this was one of the all-time great Real Madrid sides. Completely dominant in Spain, but Milan had completely dismantled them in Europe. It was Los Blancos’ greatest humiliation.

And so to the final. While Steaua Bucharest may not be the most glamourous of names these days, they were European Cup winners in 1986, and were even stronger three years later, led by Romania legend Gheorghe Hagi.

But Milan played them off the park. Steaua barely laid a glove on Milan, and they were 3-0 down at half-time, with a fourth being added as soon as the second half began. Braces from Van Basten and Gullit sealed a comprehensive win, affording Sacchi the luxury of withdrawing the talismanic Gullit before the hour mark. 

It was a masterclass from Sacchi and his men. The European Cup final had turned into a procession, and Milan were European champions again.

And it wasn’t done in the stereotypical Italian manner. Sacchi had transformed Milan, playing a brand of football not seen by Italian sides. 

The following season would see the Rossoneri fall short in the title race, being overthrown by Maradona’s Napoli late in the campaign. With nine games left, Milan had a six-point lead (in the two-points-for-a-win era), but a loss at Verona in the penultimate game of the season would cost Milan the Scudetto. 

Nevertheless, Milan had the consolation prize of another European Cup final to contest. Milan had knocked out Real Madrid once again, as well as Bayern Munich after extra time in the semi-final, and set up a clash with Benfica, runners-up two years earlier. 

An imperious Baresi ensured their clean sheet remained intact, while Rijkaard, surging through midfield, would poke home the winner.

Benfica, like Steaua Bucharest before them, were no match for Milan, who wrote their name into footballing immortality – the Italian media nicknamed them The Immortals – becoming the eighth team to retain the European Cup.

1991 would see Milan again finish second in Serie A, behind the Sampdoria side featuring Roberto Mancini, Gianluca Vialli and Pietro Vierchowod – who’d reach the European Cup final the following season. They would also be knocked out in the quarter-finals of the European Cup by a Jean-Pierre Papin-inspired Marseille.

The trophyless season combined with friction between Sacchi and Van Basten brought about the end of the Sacchi era. After a league title and two European Cups, Sacchi was dismissed by Berlusconi, leaving under a cloud. 

Ironically, Sacchi felt that after limited evolution in his time, revolution might be needed. Revolution did come, but it began with his job.

Sacchi would be replaced by Fabio Capello – almost as controversial an appointment as Sacchi himself. With no real football management experience, Capello had spent years working under Berlusconi, and was seen as little more than a Berlusconi stooge; a far cry from the Capello the football world would get to know over the next 25 years…

But Capello would stamp his authority on the squad immediately, guiding them to the Scudetto once again, but doing so without losing a single game. 

Van Basten scored 25 goals on his way to being named Capocanonniere for the second time, as Milan’s goal difference of +53 was more than twice as good as their nearest rivals. 

After their back-to-back European successes, they were the Immortals. Now, they were the Invincibles.

Sadly, it was the last full season the Milanisti would be treated to the greatness of Marco van Basten. He would spend half of the following season on the touchline – with the ankle injury that would bring his career to a heartbreaking, premature end – and it's when Milan’s form nosedived. 

With Van Basten that season, Milan recorded 10 wins and five draws, in which he scored 13 goals. Without Van Basten, Milan’s record read: eight wins, nine draws, two losses.

1991 Ballon d’Or winner Papin proved a capable replacement, matching Van Basten’s goals, as the revolution that Arrigo Sacchi craved had finally begun.

Papin arrived the previous summer, breaking the world transfer record, which Gianluigi Lentini did himself soon after, and the relaxation of rules around foreign players (teams could still only name three in a matchday squad at a time, but could have as many as they wanted at the club) meant they were joined by Dejan Savicevic and Zvonomir Boban. 

Capello would navigate the rules around the foreign players, employing a novel squad rotation policy, largely unheard of at a time when teams could only make two substitutions. 

Capello would also have to navigate European commitments unlike in his maiden campaign, but Milan would stroll to the title, despite winning just one of their final 13 games, such was the lead they’d established.

The newly-formed Champions League however, would see Milan lose in the final to Marseille, a final shrouded in controversy. 

Aside from feeling they perhaps deserved to win the game, Milan were hit by the news that Marseille had been found guilty of partaking in match-fixing, bribing opponents to go easy on them in Ligue 1 in the run-in to the Champions League final.

On top of that, Van Basten would also suffer another, this time career-ending, ankle injury in the final. 

The revolution in Milan would continue, with the side at something of a crossroads. 

The formidable back four of Tassotti, Baresi, Costacurta and Maldini would commence their sixth campaign together, but Tassotti and Baresi were well into their 30s, with the former soon to be replaced by Christian Panucci.

More importantly, the Dutch trio that inspired them to their successes from the late 80s were separated.

Ruud Gullit, somewhat ostracised by Capello (and was omitted from the 1993 Champions League final) was loaned to Sampdoria, Frank Rijkaard went back to Ajax on a free transfer, while Van Basten would miss the whole season through injury.

The great Milan side was coming to an end. But they had one final card left to play.

Papin wasn’t suited to Capello’s style of football, while Gullit and Van Basten were no longer at his disposal. Short of attacking options, the Italian shifted dramatically from the side that had scored 74 and 65 goals in the previous two seasons. Milan would score a mere 36 in 34 games. 

But the title would be won by that legendary back line in their final season as a quartet, aided by new signing and future Milan great, Marcel Desailly. 

Milan kept seven straight clean sheets to start the season and would keep 22 in total across the campaign. They conceded more than once in just two games all season, the first of which was to Sampdoria with – of course – Ruud Gullit scoring a third, decisive goal in the 78th minute against his old club.

Changes to the offside and backpass rules in 1990 and 1992 opened the floodgates somewhat to a previously conservative Serie A. 

Serie A goals per game:

The 1984/85 season averaged 2.1 goals per game, dropping to 2.06, then 1.93, before steadily increasing from 2.1, 2.11, 2.24, 2.29, 2.27, 2.8 and eventually 2.42 in 1993/94.

Yet Milan would concede just 15 goals in the league to win a third straight Scudetto.

Part of the thinking behind the managerial change from Sacchi to Capello was that as brilliant as Sacchi was, his style took too much of a toll on his players. They could only be at their peak sporadically – perfect for a side who’d win back-to-back European Cups, but not perfect for a side who’d fallen short in three straight Serie A campaigns.

Capello was the opposite. He’d been able to maintain a level throughout a season, winning the league in all three seasons, but the Champions League would be the litmus test. His side fell at the final hurdle, failing in his first attempt at European glory.

They wouldn’t fail at the second attempt.

Johan Cruyff’s return to Barcelona in the late 80s coincided with them overthrowing Real Madrid as Spanish champions, winning La Liga in 1991, 1992, 1993 and 1994, winning the European Cup in 1992.

Their Spanish core was supported by Ronald Koeman, Ballon d’Or winner Hristo Stoichkov and FIFA World Player of the Year Romario, though UEFA rules meant Michael Laudrup was left out of the Champions League final.

Barca were clear favourites; aside from their pedigree, Milan were without the suspended centre-half pairing of Baresi and Costacurta, with Van Basten still injured, and Lentini – still the world’s most expensive player – was also injured.

But Milan ran riot. Barcelona’s Dream Team were played off the park as Capello’s men won 4-0, crowned European champions for a fifth time. 

Across seven seasons, Milan won four Serie A titles and three European Cups/Champions Leagues, assembling some of the best players the world has ever seen, working under some of the best coaches the world has ever seen.

They were Immortal. They were Invincible. They were incredible. 

Liam Williams

• A.C. Milan
• The Greatest
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