The Greatest Teams in Football History - Week Eight: AC Milan (1988-1994)

This is the seventh in a series of ten articles, released weekly, counting down the ten greatest teams in the history of football. The teams were selected based on the trophies they won, the cultures they created, and the impact they had on the game of football.

The Countdown:

10. Liverpool (‘75-’84)

9. Bayern Munich (‘67-’76)

8. France (‘98-’00)

7. Manchester United (‘95-01)

6. Real Madrid (‘56-’60)

5. Spain (2008-2012)

4. FC Barcelona (2008-2012)

AC Milan 1988-1994


Associazione Calcio Milan – a name synonymous with the greatest trophies, the greatest players, and, after four years from 1988-1991, the greatest football ever played. 

Today, AC Milan is a symbol of greatness in the beautiful game. Having won eighteen Serie A Championships, seven Supercoppa Italia’s, and 5 Coppa Italia’s AC Milan stand astride Juventus as arguably the most excellent team in the history of Italian Football. In Europe, however, AC Milan sits at the head of the table. Having won the second most European Championships and Champions Leagues – seven – few teams dare to put themselves in the same sentence as the Rossoneri. 

In 1986, however, AC Milan’s achievements had been banished to the depths of their history. With memories of their two European Championships from 1963 and 1969 fading from memory, Milan was a disgrace to their storied history. Six years earlier, Milan was a central figure in the 1980 Totonero Scandal in which teams were accused of selling matches to high bidders. As punishment, the team was relegated to the Serie B, Italy’s second division. Throughout the mid-’80s Milan struggled to escape the Serie B only to have their woeful football exposed by experienced Serie A squads. Remember, in the ‘80s and ‘90s, the Serie A was the pinnacle of Football’s major five leagues. The Napoli of Maradona, the Inter of Matthaus and Klinsmann, and the Sampdoria of Mancini and Vialli dominated Italy and Europe playing defensive, suffocating football. Compared with these Ferrari’s, AC Milan was a bicycle with deflated tires – wobbling in place while trying to match the pace of their opposition. Milan was caught in an impossible struggle and there appeared no way out. 

AC Milan was desperate for a savior, someone to drag them back to the top of Italian football and place them in position to challenge Europe’s greats. In 1986 – their savior arrived – though not in the form many expected. His name was Silvio Berlusconi. A Millionaire who made his fortune as a media tycoon, spreading his name throughout tabloids and newspapers as a philandering scandal-monger, this future politician bought AC Milan in an attempt to bring stability back to his beloved club. No, this was not a shrewd billionaire, hell-bent on turning a club into a profitable business. This was a man who wanted the best football to be played in his favorite city, by his favorite club, and in his favorite uniforms. Have you ever heard of anyone more Italian? 

Silvio Berlusconi - the savior.

Silvio Berlusconi - the savior.

Looking back on the success his arrival preceded, perhaps Berlusconi was the only possible solution. For a club with a troubled past of equal parts corruption and magnificence, they needed an ego at the helm that matched their persona. 

If Berlusconi’s buyout was AC Milan’s first-step back towards greatness, the hiring of Arrigo Sacchi was the second and by far the most critical. 

In 1987, when Berlusconi announced the club’s new manager, however, the critics could not have been more vocal in their opposition. 

Sacchi, a complete outsider to fans of Italian football, could not possibly be the pilot of this storied club. At 41 years old, the Serie B Parma manager’s greatest achievement was knocking AC Milan out of the Coppa Italia the previous season. To think that such a man was worthy of taking the reins of Milan was unthinkable. 

Arrigo Sacchi - 1989

Arrigo Sacchi - 1989

“They asked me – how can you coach winners if you’ve never won anything yourself,” says Sacchi. Fond of playing poet, Sacchi responded to his critics, “I didn’t know to be a jockey you must first be a horse.” 

Though many fans of Milan criticized Sacchi’s appointment, he was dedicated to proving them wrong. After all, Berlusconi’s decision to give him the job was, in Sacchi’s fantastical mind, a symbol of the Italian spirit. He says, “Berlusconi made a real Italian story come true – he gave a Ferrari to a complete stranger.”

Though Sacchi had been appointed to his dream job, Berlusconi was determined to fulfill a dream of his own – assembling the greatest football team in the world. To do so, the new owner was not sparing any cents, immediately splurging a record $10 million on PSV striker Ruud Gullit. Shortly after his arrival, Gullit was joined by his Dutch International teammate Marco Van Basten. Though both forwards were recruited for their successful history, the Dutch imports would play critical roles in Sacchi’s tactical revolution.  

Sacchi deploying his tactics.

Sacchi deploying his tactics.

Given the extent to which Sacchi embraced his role as an outsider of Italian football, it only made sense for his footballing philosophy to be equally foreign. For Sacchi, Italian football was too dull and slow. At the time, Italian football centered around a rigid backline of man-marking defenders that played behind a “libero.” Similar to Beckenbauer’s “sweeper” position, the “libero” would provide an outlet for defenders and act as the engine that started the attack. As for scoring goals, the onus was heaped on individual skill and the creativity of the number 10. Player’s like Maradona embraced the role, using the freedom of a solid defense behind them to express their ingenuity. For most Italian sides, once their forward had scored, the goal of the team was to defend, defend, and defend some more. This was Italian football, and Arrigo Sacchi absolutely hated it. 

Sacchi desired to turn this boring style of football on its head. He said of his intention, “In Italy, you score a goal, and everyone defends the lead. I’d say – when we score a goal – we keep attacking.” Though he demanded offensive production from his team, Sacchi did not neglect his defense – for Sacchi, defense and offense were interchangeable. He said of this philosophy, “The only way you can build a side is by getting players who can play a team game – eleven players active in every moment of the game, both in the defense and the attack.”

To achieve such dominance on both ends of the pitch, AC Milan played a zonal marking 4-4-2. The distance between the attacking, midfield and defensive lines was never more than 20 to 25 meters. Such congestion demanded a high press that linked the defense with the attack. Executing Sacchi’s tactics to perfection, AC Milan suffocated their opposition.

Though his “total football” approach was revolutionary in Italy, Sacchi saw his philosophy as a continuation of the great teams that came before him: “I saw that all the great teams to be great had something in common. They all looked to dominate on the pitch – dominate play and control the game at all times.” To pull off this demanding tactic, however, Sacchi required the services of equally great players. 


In attack, Van Basten led the line with Ruud Gullit trailing behind him in a center forward position. The all-Dutch attack that dominated International football for the Netherlands was equally lethal at club level. For Sacchi, both players were perhaps the most vital to allowing Milan to play his style of football. For context, Gullit won the Ballon d’Or in ‘87 with Van Basten winning it in ’88, ’89, and ’92. 

Sacchi said of Van Basten, “He remains the best striker of all time in my opinion. No other forward has worked as hard for the team as Marco did at Milan. Above all, however, I remember him for his elegance, his grace, and his incredible ability.” Though Van Basten was sidelined due to injury for much of his first season at Milan, the striker proved deadly in the years that followed. When he wasn’t scoring possibly the greatest goal of all time in the final of the European Tournament for his National team, Van Basten played the role of workhorse for Milan’s attack. In 201 appearances for Milan, Van Basten scored 125 goals. 

The man that played behind him, however, was even better. For Sacchi, Gullit was the answer. The greatest player at AC Milan? The most creative footballer of his era? The driving force in Milan’s style of play? Gullit did it all. 

Ruud Gullit

Ruud Gullit

Sacchi says of Gullit’s leadership, “Gullit was the leader. He had a very strong character. For me, he was number one. He helped me a lot, especially to change the team’s mentality.” Though Sacchi praised Gullit for his role in the dressing room, the Dutch forward maintained a level of play that awarded praise from football’s greats. 

After watching Gullit play in the final of the 1990 Champions League, George Best said of the forward, “He is a great player by any standards. He's not afraid to do things with the ball. And he looks as if he's enjoying every second of it. By my reckoning that's what makes him an even better player than Maradona."

Sacchi’s midfield four consisted of Colombo, Ancelotti, Rijkaard, and Donadoni. Rijkaard, the third Dutch international who arrived a season after Gullit and Van Basten was to many the most vital member of the squad. 

Rijkaard’s Dutch teammate and future managerial opponent Ronald Koeman said of Sacchi’s central midfielder, “His move to Milan in 1988 was the making of him – Arrigo Sacchi transformed him into an aggressive, world-class holding midfielder who could score goals, too. Dunga, Desailly, Keane, and Vieira all performed that role brilliantly, but Frank is the best holding player ever.”

Gullit, Van Basten, and Rijkaard

Gullit, Van Basten, and Rijkaard

Yes, Sacchi had three of the greatest Dutch players in the country’s history throughout the spine of his squad. Their goal-scoring and overwhelming attacking play swarmed opposing sides, forcing every team in Europe to reconsider their pre-conceived notions of football. 

Oh, and this article hasn’t even mentioned Sacchi’s defense, particularly, his defender – Paolo Maldini – the greatest defender in the history of football. 


In his professional career that spanned from 1985 to 2009, Paolo Maldini tallied 902 appearances for AC Milan, the second most appearances in the history of European soccer. This was a man who defended against the greatest players of the last forty years, all at the peak of their talent. From Maradona to Messi, from R9 to CR7 – Maldini defended against them all and always came out on top. 

In previous articles, players of great squads have been defined as the best passers, the most ruthless finishers, and the most creative dribblers. Maldini, however, stems from the alien breed of players – of men – who achieve mastery in every aspect of the game in which they are involved. A brilliant reader of the game, Maldini often kept clean sheets without making a single tackle. Instead, he pulled the strings of Milan’s defense, shouting instructions and motivating his teammates. Maldini, however, was also a ferocious tackler who tormented attackers with perfectly-timed sliding tackles and inch-perfect positioning. 


His discipline and passion for his club and for his nation were consistent. Not once did a supporter of Milan or Italy question their leader’s intentions. It is these qualities of his personality along with his domination of the football pitch that established his legacy. 

That Maldini became the greatest defender of all time playing for Milan, however, was not down to fate, it was down to blood. Sir Alex Ferguson clashed with the Maldini-Milan connection when he attempted to sign Paolo to Manchester United in the early ‘90s. Ferguson recalls his meeting with Paolo’s father Cesare Maldini being rather short: “I got a shake of the head. That’s all I got. He said, ‘my grandfather was Milan, my father was Milan, I’m Milan, my son is Milan’.”

With the transfer-market in its current chaotic state it is difficult to imagine a player ever establishing a legacy so intertwined with a country, city, and club like Paolo Maldini did with Italy, Milan, and the Rossoneri. 

With the players to perfect his tactical system, Sacchi unleashed his Milan side on the rest of the Serie A. Throughout their first season, AC Milan confused opposing sides with their ambitious attacking play. Sacchi’s foreign system worked wonders, giving AC Milan a golden opportunity to go top of the league in a match against Napoli at the tail end of the season. Diego Maradona and Napoli, however, were no easy matchup. After winning the inaugural Serie A season the previous year, they had kept their place at the top of Italian football. If Napoli won the game, they would seal the title for themselves. 

In front of 90,000 Napoli fans at the San Paolo Stadium in Naples, AC Milan had to beat the title holders if they wanted to have a chance at winning the Scudetto for themselves. That day, two goals from Pietro Paolo Virdis and another from Marco Van Basten gave AC Milan a 3-2 win over their title rivals. Milan had secured a critical victory. The most significant moment of the match, however, occurred not on the pitch but in the stands. As the referee blew the final whistle, the Napoli fans rose to their feet and began applauding the AC Milan players. Milan’s football was so revolutionary and refreshing to Italian football that even opposing fans could not help admiring their excellence. 

For Sacchi, the happiness of the supporters, whether or not they were from Milan, was his real goal: “My aim was to play great football, but my greatest objective was to make people enjoy themselves.”

Two weeks later, AC Milan traveled to the neighboring city of Como where they needed only a draw to be crowned champions. After ninety minutes, the scoreboard read 1-1: AC Milan had just won their first Scudetto since 1979. Though the players celebrated with their traveling fans, they returned to Milan that night to present their trophy to the red and black half of the city. That evening, the club opened the San Siro to the supporters, inviting their fans to fill the stadium and see their team for a final time that season. Standing on the sidelines, Berlusconi and Sacchi looked on as Gullit, Van Basten, Virdis, and Maldini walked around the grounds, displaying their trophy to 80,000 screaming Milan fans. In a single season, Berlusconi and Sacchi had achieved the beautiful football they wished to create and were already adding to the club’s trophy collection – but this was just the beginning. 

Milan celebrate winning the 1988 Scudetto.

Milan celebrate winning the 1988 Scudetto.

The following summer, Berlusconi reinvested in his squad, adding the Dutch International Frank Rijkaard to the core of the Milan midfield. Rijkaard had played a crucial role in the Netherlands success in that year’s Euros, helping fellow Dutch teammates Gullit and Van Basten beat the USSR 2-0 in the final.

Returning to Milan after their summer break, the Rossoneri set off on their second campaign determined to end the year with even more trophies than before. Having conquered Italy, Europe became the focus of their domination. 

In the European Cup, Milan got off to a flying start, trouncing Bulgarian club Vitosha 7-2 on aggregate. Their next match, however, set them up against a far more challenging opponent from the eastern bloc – Red Star Belgrade. 

The infamous fog match.

The infamous fog match.

Having drawn the first leg of the tie at home 1-1, Milan traveled to Serbia losing on away goals. Though Red Star scored early in the second leg, God was on the side of AC Milan. That day, a dense fog swarmed the pitch, preventing players from seeing more than ten feet in front of them. In a series of scenes that are among the most alien and unusual in the history of football, the game was called off. Though Red Star was ahead, the game was scrapped. The teams would replay the game the following day. 

Eager to change their fortunes, Milan battled back, scoring in the 34th. Red Star responded with a goal of their own and, after the final whistle blew, the match was sent to penalties. Having been saved once by God and once by Van Basten, the Rossoneri were destined to advance. Rijkaard secured their fate, scoring the winning penalty to complete Milan’s great escape. 

Their road grew only more difficult, however, as Milan hopped from the frying pan of Red Star into the fire of Real Madrid. For any normal side, drawing Real Madrid in the European Cup was a death sentence. But AC Milan was different. They saw the draw as an opportunity to prove why they were the most excellent team in the world. And they did not let the opportunity go to waste. 

After securing a draw in the first leg in Madrid, AC Milan’s own San Siro would be the scene of the club’s greatest European performance in their history. In the 19th minute, the man who would later lead both Milan and Madrid to Champions League victories as a manager – Carlo Ancelotti – lashed home the opener with a strike from outside of the box. Six minutes later, Milan doubled their score through Frank Rijkaard. 

While other Italian sides would have immediately retreated, happy to stifle the Spaniards for the following 81 minutes, AC Milan saw blood in the water, and they were out for the kill. 

Recalling his team’s performance, Sacchi emphasized, “That team was different from other Italian teams because it always wanted more. We were two up and wanted another. At three nil, we wanted four nil, at four nil we wanted to score a fifth. And, if the match had gone on, we would have wanted more.” 

AC Milan ended the match with five goals. Ancelotti, Rijkaard, Gullit, Van Basten, and Donadoni all penciled their names onto the scoresheet. For Sacchi, the moment was pure bliss, “It was a fantastic occasion for us. For me, it was the moment when Milan astonished the world of football.” 

After such a performance in the semi-final against Real Madrid, the result of the final was a foregone conclusion. On the 24th of May, 1989, AC Milan beat Steaua Bucharest 4-0 in front of 100,000 fans at the Camp Nou in Barcelona. Gullit and Van Basten scored two goals apiece, completing a dominating performance that reflected their position in European football. 

Sacchi and Berlusconi celebrate the 1989 Cup victory.

Sacchi and Berlusconi celebrate the 1989 Cup victory.

AC Milan and Arrigo Sacchi had achieved nirvana. Literally. Sacchi said in an interview many years later, “When we won the cup the first time I experienced something I’ve never experienced before in life or in football, and it’s something I recommend for everyone to try to achieve: waking up the next morning with that sweet taste of success in your mouth.” 

But Berlusconi bought AC Milan to create the best squad in the world, not merely in Europe or Italy. In December of 1989, AC Milan took on the Colombian side Atletico Nacional in Tokyo in the final of the Intercontinental Cup. Milan won the difficult match thanks to an Evani free kick in the 119th minute. AC Milan had reached the peak of world football, and they were determined to hold that position for many years. 

The 1989/1990 season proved the most difficult of Sacchi’s reign. The squad was plagued with injuries, forcing Sacchi to replace up to seven first-choice players. A severe knee injury to Ruud Gullit prevented the Dutch forward from competing in all but two league matches. The absence of such crucial players dulled the spear of Milan’s attack, causing them to suffer in the league. After Napoli ran away with the title in early 1990, Milan turned all of their attention to Europe where they had been drawn yet again with Real Madrid, this time in the first knockout round of the European Cup. 

A 2-0 victory at the San Siro in the first leg with goals from both Rijkaard and Van Basten was enough to push Milan past their Spanish rivals. In the semi-finals of the competition, Milan would have to take down yet another European giant, Bayern Munich. 

Though Milan won the first leg at home 1-0, they headed into the reverse fixture in Germany with a severely weakened squad. After ninety minutes, Munich led the game 1-0, level with Milan on aggregate. In the first minute of the second half of extra time, Stefano Borganovo chipped Bayern keeper Raimond Aumann to give AC Milan the aggregate lead and the crucial away goal. Ultimately, Bayern Munich won the match 2-1, but AC Milan had won a place in the European Cup Final. 

Vienna was the sight of the 1990 European Cup final that pitted AC Milan against the runners-up from two years prior – Benfica. 

Though their victory the previous year had been AC Milan’s first European Trophy in decades, the 1990 tournament was by far the more difficult affair. The AC Milan players were battered and exhausted from the twelve months of constant competition. Sacchi knew his players were not prepared for the cup final, and so he decided to make a critical adjustment to his team sheet – he chose to start Ruud Gullit for the first time in ten months. 

In a post-match interview, Milan goalkeeper Giovanni Galli explained the shocking effect Gullit’s appearance had on the Benfica players: “There were two ways for them to look at it. On the one hand, caution: ‘because Gullit is playing, let’s be careful.’ On the other hand, with him having been out for ten months, they’d be thinking, ‘he’ll not be as fit as the others.’” 

Though Benfica’s disciplined organization and solid defense proved immensely tricky for AC Milan to breakdown, the weakened Rossoneri managed to do the thing that unites all great teams – win. In the second half, with the score stuck at 0-0, Sacchi told Van Basten to drop behind Gullit into AC Milan’s midfield, jamming the gears of the Benfica machine. In the 68th minute, the tactical change allowed Van Basten to receive the ball 15 meters above the Benfica box. Seeing the forward receive the ball, the Benfica defenders collapsed onto him forgetting to mark Frank Rijkaard who tore into the space they left free. Van Basten spun the ball into Rijkaard who tore into the box, finishing the goal with a deft flick past the Benfica keeper. The goal was all AC Milan needed. They were European Champions. Again. 

Rijkaard against Benfica

Rijkaard against Benfica

But for Sacchi, the victory marked the end of the road. Though he would retain his Intercontinental Cup title with AC Milan later that year, Sacchi decided the time had come for him to leave the club: “I was tired. I asked for everything, and I gave everything I had. I could no longer give my all. I was looking for a new challenge because I’d won everything.”

Sacchi was replaced by Fabio Capello who had managed Milan for a brief spell before Sacchi’s appointment in 1987. Taking over as manager of a team that had won two consecutive cups, Capello realized, would not be an easy feat. 

Though Capello was unpopular with the fans throughout his first season with Milan, he provided stability in the wake of Sacchi’s departure. He achieved the smooth transition by trusting the players that Sacchi had turned into legends of the modern game while keeping faith in the quality of football that his predecessor demanded. And, before long, Capello returned the club to their trophy-winning ways. 

In 1992, Capello returned the Serie A trophy to AC Milan, and he did so in style. Milan won the league without losing a single game, a feat that had only been achieved once before in Italian history. But their unbeaten streak did not end there. Capello said of their dominance, “I had the same opinion as Berlusconi. I wanted to keep the side together. And that team became known as the invincibles because we went 58 games unbeaten. That’s a record.” 

Though they lost the 1992 final of the newly named “Champions League” to Marseille, Capello had the squad primed for one final run to achieve victory in Europe. After winning the Serie A in both 1993 and 1994, Milan returned to the final of the Champions League. This time, they faced Johan Cruyff’s Barcelona “dream team.” 

Entering the match, Milan knew that their decade of dominance had reached its end. Gullit and Rijkaard had departed the previous year, and Sacchi’s total football no longer appeared as vibrantly at the San Siro. Johan Cruyff seemed hell-bent on sending Milan into the grave and repeatedly made comments to the press before the match, remarking on the fact that to win the game, Barcelona merely had to put on their uniforms. 

Milan forward Daniele Massaro remembered Cruyff’s comments as the spark that ignited Milan’s performance: “Every time we read the papers and watched on television what Cruyff and the Barcelona players were saying, we just became more and more determined.”

Shortly after the match began in Athens on May 18th, 1994, it became clear – AC Milan would be digging Cruyff’s grave, and Daniele Massaro was the man with the shovel. 

Massaro scored twice in the first half, shocking the Catalans with his clinical finishing. In the second half, goals from Dejan Savićević and Marcel Desailly doubled Milan’s lead. Milan’s era of dominance had ended the way it began – in victory. Their 4-0 victory over Barcelona, however, resembled the club’s period of magnificence in more ways than one. 

Milan celebrate victory in 1994.

Milan celebrate victory in 1994.

For Fabio Capello, Milan’s greatness was not defined by a single player or a tactical philosophy. Greatness, he believed, was a collaboration of individual brilliance and inspired dedication to a city, a club, and a jersey. Capello said, “In that game, those players reached heights never seen before. We could have beaten anyone. If you want to play music at the highest level, you need true maestros who will form an orchestra good enough to perform all over the world. And that team was exactly that.”

The dream that incited Silvio Berlusconi to buy the corrupt and struggling AC Milan in 1986 had been achieved. Through the genius of Arrigo Sacchi and the talent of Maldini, Gullit, Rijkaard, and Van Basten, AC Milan became artists of possibly the most beautiful and lethal football the world has ever seen. AC Milan do not have the most trophies in Italian football, Juventus does. Milan also do not have the most European trophies, that record belongs to Real Madrid. But in the late ‘80s Arrigo Sacchi’s AC Milan became the standard for European football supremacy. Today, the greatest clubs look up to Milan as a reference for their own achievements, hoping that one day people will speak their club’s name in the same sentence as the revolutionary, dominant, and inspiring Associazione Calcio Milan.