Mon 28 March 2022 | 10:30

The Golden Generation of Milan

With 7 championships in European Cup/Champions League, AC Milan is the second most successful club in the tournament and one of the most popular football teams around the world. Stay tuned with us to deep dive into club’s history and review the golden generation of Milan.

AC Milan was founded in the December of 1899 as the English football player Herbert Kilpin and his fellow English businessman Alfred Edwards decided to create a football and Cricket club in the city of Milan, Italy. Kilpin had a player-manager role at the early years of the club and won the club’s first two national trophies. For the following decades, Milan was a mediocre side in Italy’s top flight until in 1950s when they made a name for themselves by winning 4 Serie A titles which was followed by 2 European Cup championships in the decade after that.

Now Milan was one of the most decorated sides in Italian football but following a scandal in early 80s, the club got relegated to Serie B for the first time in its history as a punishment. While Milan was going through its darkest years and when the club was facing bankruptcy, the Italian politician and entrepreneur Silvio Berlusconi bought AC Milan and prevented its downfall. With Berlusconi’s investments, Milan once again emerged as powerhouse in Italian football and that was how

the golden generation of Milan

started to shape up.

When Was the Golden Era of AC Milan?

Almost immediately after Berlusconi’s acquisition of the club, Milan rebuilt itself and became a regular title contender both on domestic and international level. We could say that Milan had two golden generations in its history. The first one was when Arrigo Sacchi-

one of the best Italian coaches ever

, joined Milan in 1987. As a genius tactician, Sacchi’s Milan team is renowned as one of the best football teams in history of the sport that introduced some revolutionary tactics both on attacking and defending phases of the game.

With Sacchi, Milan reached two back-to-back European Cup finals in 1989 and 1990 and won both of them against Steaua București and Benfica respectively. In 1991, Fabio Capello replaced Sacchi on Milan’s bench and he also led the Rossoneri to two consecutive European Cup finals. Capello lost the first final to Marseille in 1993 but he managed to win the second one against Johan Cruyff’s Barcelona in 1994 which was Milan’s fifth championship in the competition. In addition to European successes, 5 Serie A titles in the 90s was the highlights of the first golden generation of Milan who had some greatest Milan legends in it.

Names like Franco Baresi, Alessandro Costacurta, and the legendary Dutch trio of Frank Rijkaard,

Marco van Basten

, and Ruud Gullit were the key players of the golden generation of Milan in 80s and 90s. But in this article, as you would guess from the cover photo, we are focusing on the latest edition of the golden generation of Milan which took place in the early 2000s. A wonderful team that had some of the best football players of that decade in its squad and managed to create so many great moments in the history of European football. 

A Fresh Start with Carlo Ancelotti


won its last title of 90s with Alberto Zaccheroni as head coach who led them to win Scudetto (the traditional name of Serie A title) in the 1998-99 season. Zaccheroni carried on in Milan but it seemed like that he just can’t take them to the next level. During the 2000-01 season of Champions League, Milan got eliminated in the second group stage of the tournament and only one day after that, he got dismissed by the club in midseason. The 2001-02 season started with the Turkish manager Fatih Terim being at charge. But he was not given the time and trust needed to create a winning team and Milan fired him only five months into the season.

The constant managerial changes were worrying Milan fans and also made life difficult for every new manager that set foot at the club. In November of 2001, Milan appointed Carlo Ancelotti who just had a two-year spell at Juventus and only managed to win a UEFA Intertoto Cup in 1999 with them. The Italian coach had an average debut season and qualified for next season’s Champions League football. But Silvio Berlusconi was not happy with him due to his relatively defensive style of play. Therefore, Ancelotti made some key changes for his second season at the club and gained trust from Milan board.  

Sixth European Championship

Carlo Ancelotti himself had an important role in the golden generation of Milan during 80s and now he was returning to the club to create his own dream team. Prior to his first full season at Milan, Ancelotti enjoyed a successful summer transfer window which Milan spent a lot of money to gather around some of the finest football players in one team. Alessandro Nesta, Clarence Seedorf, Jon Dahl Tomasson, and Rivaldo arrived at

San Siro

in that summer and now Ancelotti had everything he wanted to bring home some trophies for AC Milan.

Although Milan was sitting at top in Serie A table at midway point of the 2002-03 season, they couldn’t protect their lead and finished third in Serie A as Juventus won the Scudetto. On domestic cup as known as Coppa Italia, Milan won its fifth and as of today last championship beating Roma in final. But the biggest achievement of 2002-03 season came from the European front. Milan had a shaky start to their European campaign as they progressed to group stage by defeating the Czech side Slovan Liberec only by away goals rule. 

Milan improved throughout the season and topped Group G of Champions League- where Bayern Munich surprisingly finished at the bottom with two points. On the second group stage, Milan gathered 12 points- similar to their previous group stage results, and advanced to quarter-finals where they beat


3-2 thanks to Jon Dahl Tomasson’s last minute goal. They met city rivals Inter in semi-finals and made their way to final thanks to Shevchenko’s away goal in a 1-1 aggregate score. The final was taking place at Old Trafford against Ancelotti’s former club, Juventus. After 120 minutes of tedious football between two Italian giants, it was down to penalties to decide the winner.

Penalties was a heroic battle between the two goalkeepers: Juventus’s Gianluigi Buffon and Milan’s Dida. Buffon denied two shots that came from Seedorf and Kaladze but on the other hand, the Brazilian Dida managed to deny three shots from Trezeguet, Zalayeta, and Montero. Finally, Shevchenko converted Milan’s fifth kick and that was how Rossoneri claimed its sixth Champions League title almost ten years after winning the fifth one with Fabio Capello. 

The Infamous Istanbul Final

The 2003-04 season was a roller-coaster ride for Milan fans. They lost Italian Supercup to Juventus on penalties, but then managed to win European Supercup beating Porto. They win their 17th Serie A title with 82 points- 11 higher than the runner-up Roma, but suffered from a ridiculous comeback in the quarter-finals of Champions League. They won the first leg against

Deportivo La Coruña

4-1; but on the second leg the Spanish side somehow managed to score 4 goals and win the tie 5-4 against the reigning European champions.

Milan also lost that season’s Intercontinental Cup clash against Boca Juniors on penalties which meant that they failed in 4 out of 6 competitions across 2003-04 season. The 2004-05 season was even worse. Milan started by winning Italian Supercup against Lazio with a 3-0 win but they finished second in Serie A, 7 points shy of Juventus’s 86 points. On Champions League, Milan topped their group for the third consecutive year and face Manchester United in round of 16. Two similar 1-0 wins sent them to quarter-finals for another European Milan derby.

After a 2-0 win in first leg, the second leg match was abandoned due to Inter fan’s hitting Milan’s keeper Dida with a firework in 72nd minute. Eventually Milan was handed a 3-0 win and saw themselves in semi-finals against the Dutch side PSV Eindhoven which they came on top thanks to away goals rule in a 3-3 draw. Atatürk Olympic Stadium in Istanbul was the final’s venue where Liverpool was going to face up against the

best Milan team


The match looked done and dusted at the end of first half as Paolo Maldini scored the fastest goal in a UCL final which was followed by Hernan Crespo brace which gave Milan a 3-goal lead prior to second half. But in the span of 6 minutes, Liverpool bagged 3 goals through Steven Gerrard, Vladimír Šmicer, and Xabi Alonso and now the game was on. Neither side managed to score again and it was up to penalties, again. This time Milan was not lucky enough and lost the shootouts to Liverpool 3-2. That concluded one of the craziest finals in the history of European football which Milan was at the losing end of it.

Devil’s Revenge

Despite getting some sticks because of giving away huge leads in two consecutive seasons of Champions League against Deportivo La Coruña and Liverpool, Carlo Ancelotti stayed at Milan to kick off his fifth season with Il Diavolo (The Devil-Milan’s nickname). The 2005-06 season of Italian football was heavily influenced by Calciopoli scandal which affected Milan as well. Due to their involvements in Calciopoli, Milan got penalized 30 points and barely secured a qualification for next season of Champions League. Their European run ended at semi-finals as Barcelona defeated Milan with a 1-0 aggregate score.

Calciopoli was still hunting Milan as they started the 2006-07 season with an eight-point deduction as punishment. Ancelotti’s team finished the league at fourth place with only 3 points more than Palermo who was fifth. People were starting to doubt that if

the golden generation of Milan

is able to win another trophy at this point; and Milan gave them an answer. AC Milan finished first ahead of Lille in their UCL group and knocked out Celtic with Kaka’s last minute sole goal in the second leg. Bayern Munich was the next opponent and Milan won 4-2 on aggregate. 

In a thrilling semi-final Milan came superior versus Manchester United with a scoreline of 5-3 at the end of both legs. Final was a showdown between Milan and Liverpool, the perfect opportunity for Milan to seek their revenge after losing the Istanbul final in 2005. It was Milan’s 11th and as of today last appearance in a European Cup/Champions League final which was going to take place in OACA Spyro Louis Stadium, Athens, Greece. The Italian number 9

Filippo Inzaghi

scored two goals at the end of each half and Liverpool only managed to respond to one of them as Dirk Kuyt scored a late consolation goal.

That was Milan’s seventh European championship which made them the second successful club in Champions League behind Real Madrid who had 9 titles to their names back then. During the 2007-08 campaign, Milan won UEFA Super Cup title beating Sevilla to is and celebrated a FIFA Club World Cup trophy with a 1-0 against Japanese club Urawa Red Diamonds. Those were Carlo Ancelotti’s last trophies at AC Milan and also the last silverwares that the golden generation of Milan managed to bring home in 2000s. Ancelotti parted ways with Milan in 2009 to join Chelsea and just like many other Italian giants, AC Milan faced a heavy decline in the following decade. 

Key players in the Golden Generation of Milan (2000s)

Having consistency throughout seasons and keeping your best players is a huge factor in creating a winning team and that was among the main reasons that formed up the best Milan team. As mentioned above, Ancelotti began his Milan career with a busy summer transfer market in 2002. But once the foundations of the golden generation of Milan were built, it remained intact for several years and Ancelotti’s Milan had a passive approach towards transfer market.

Milan’s main formation during Ancelotti era was a 4-3-2-1 which was regarded to as the Christmas tree due to its scheme similarity to the shape of a Christmas tree. It was consisted of a deep playmaking midfielder with two hardworking fellow midfielders around him and two attacking midfielders/second strikers just behind the main striker. There were so many brilliant football players that flourished in Milan from 2002 to 2008, but to keep it short we are going to review the outstanding ones below:


Nélson de Jesus Silva simply known as Dida was a Brazilian goal keeper who started playing football from his home town club


in 1992. It was 8 years later when Milan recognized his talents and bought him from Corinthians for a transfer fee of $1.5m. Since the beginning 2002-03 season, Dida became the number one choice to guard Milan’s net as a well experienced 29-year-old shot stopper. He was a specialist in saving penalties which gave Milan the upper hand in so many decisive moments.

Obviously the most important one was the final of 2003 Champions League when he saved 3 out of 5 shots from Juventus players and was the main man of the show in winning Milan’s sixth European title. During his time at AC Milan, Dida was often renowned as one of the best goalkeepers in world of football. He stood between the posts for Milan until 2010 and is among one of the few goalkeepers in club’s history that has more than 300 appearances to their name. So, one could argue that there are not so many figures that could challenge Dida for a place on

Milan all time XI


Dida was not the only Brazilian that had a crucial role in the golden generation of Milan during 2000s. The legendary right-back Marcos Evangelista de Morais who we all know him as Cafu was also a part of Ancelotti’s team in those prosperous years. Cafu already had a successful career even before joining Milan in 2003. He started from

São Paulo

in 1989 and won 11 gold medals during his 6 years at the Brazilian club. Roma was Cafu’s first European experience as he joined the club in 1997 and became a fan favorite with more than 200 games for the Giallorossi and helping them winning their third Scudetto in 2001.

In 2003, Cafu joined Milan as a free agent which was a massive upgrade in Milan’s squad. He was 33 years old when wore the read and black Milan shirt for the first time but still he managed to perform at a world class level for the next five seasons. The two-time World Cup winner enjoyed his last chapter of professional football career at Milan and finally hanged up his boots at the end of 2007-08 season with having 166 games, 4 goals and 22 assists for Milan.

Paolo Maldini

As the only player who was a part of both golden generations of Milan in 80s and 2000s, Paolo Maldini is one of the most decorated players in European football history. He developed his skills through Milan youth academy and made his debut for the first team in 1984 as a 16-year-old prospect. Two years later, he finally earned a spot as a starter in one of the best squads that the world has ever seen. In the beginning years of his career, Maldini was mainly a Centre-back alongside one of the other

Milan legends

Franco Baresi.

Then he showed that he is capable of playing at left-back position without dropping quality. Therefore, during the golden years of Ancelotti at Milan, Paolo Maldini was playing at the left side of a four-man defense consisted of

Alessandro Nesta

, Kakha Kaladze/Jaap Stam, Cafu, and Maldini himself. Paolo remained a one-club man in his entire career and is the club’s most capped player with 902 games- almost 200 more than Franco Baresi at the second place. Maldini has won the stunning number of 25 titles with Milan including 5 Champions League and 7 Serie A trophies.

Andrea Pirlo

Milan had a dream midfield line during those years and it is not an easy task to pick only one of them. The Italian Gennaro Gattuso, the Portuguese Rui Costa, and the Dutchman Clarence Seedorf were among the best players of their generation, but we could say confidently that Andrea Pirlo was a unique midfield player who grace the pitch with his elegant and stylish footballing skills. Pirlo graduated from


youth academy and spent 3 years with Brescia senior team before joining Inter in 1998. Things didn’t go as planned in Inter and in 2001 Pirlo switched sides as he joined the city rivals Milan- just like what Seedorf did a year later.

In his debut season, Pirlo got deployed as an attacking midfielder but he didn’t fit in that area of the pitch. One of the major changes that Ancelotti made during his early years at Milan, was moving Andrea Pirlo to a deeper position just in front of the defensive line as a deep playmaker. That was where Pirlo reached to his full potential and earned the nickname Maestro. From 2001 to 2011 Pirlo was a regular starter for Milan and took part in 401 matches. He also won the 2006 World Cup with Italy when he was a Rossoneri player. 


His full name is Ricardo Izecson dos Santos Leite but football fans will remember him with his number 22 shirt which printed Kaká at the back of it. The Brazilian arrived at Milan in 2003 for a transfer fee of $9m after having his breakthrough with São Paulo. Kaká only had 21 years old when he joined Milan but he didn’t need much time to adopt to European football as he had 21 goal contributions in 40 games on his debut season.

Kaká was a creative attacking midfielder who had a perfect combination of skill, speed, and physics in his repertoire which helped him to tore down every defensive line that he played against. After winning the Champions League with Milan in 2007, Kaká won the Ballon d’Or award of both Cristiano Ronaldo and Lionel Messi. Finally, in 2009 Real Madrid spent a whopping $73m to sign him and Kaká left Milan after submitting 95 goals and 78 assists in 270 games. Kaká spent a shorter time at Milan compared to other members of the golden generation of Milan, but his extraordinary form and delightful style of play during those years was enough for fans to consider him one of Milan legends. 

Andriy Shevchenko

Milan spent $26m to sign the Ukrainian striker from Dynamo Kyiv in the summer of 1999 which was an impressive number back then. Andriy Shevchenko only needed one season to prove that he worth every penny of that money as he became Serie A top scorer on his first season in the league with 24 goals. Shevchenko was a pacey striker and lethal in front of opposition’s goal and scored some of the most memorable goals for 

the golden generation of Milan

. Just like Kaká, Andriy Shevchenko also won a Ballon d’Or trophy when he was wearing Milan colors in 2004.

Although Milan enjoyed having some legendary strikers throughout its history such as Marco van Basten and Gianni Rivera, but many will put Andriy Shevchenko on their Milan all time XI as the main striker and we could not blame them. Shevchenko and Filippo Inzaghi formed one of the most prolific attacking duos in those days of European football and both of them are amongst the top 10 players with most goals in Milan history. Inzaghi is sitting at sixth with 161 goals and Andriy Shevchenko with 175 goals is Milan’s second all-time top scorer behind Gunnar Nordahl.

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source: SportMob

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