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The history of AC Milan has seen plenty of high moments throughout club history, but some of them truly stand out above the rest. For Milan fans around the world, these five moments are ones that will always be remembered, whether they were ownership changes, big wins, or even players being signed.

The Signing of Maldini

Heading into the 1950s, AC Milan hadn’t won the Serie A title in over 40 years, and their three league titles came between 1901 and 1907. Fortunes would change in 1951 when the club won Serie A, then became a dynasty after acquiring Cesare Maldini. The defender proved to be the best in all of Italy and started his career with Triestina during the early part of the decade. In 1954, he joined AC Milan and began what would be more than a decade of dominance.

Maldini made nearly 350 league appearances with AC Milan, and during that time, AC Milan won the Serie A title five times. The club also won the European Cup and Latin Cup while Maldini was named to the AC Milan and Italian Football Halls of Fame. Maldini even went on to manage AC Milan after his playing career ended, winning the Coppa Italia in 1973.

Silvio Berlusconi Takes Over

Whether you love him or hate him, Silvio Berlusconi was absolutely instrumental in keeping AC Milan toward the top of Italian football. In the summer of 1986, Milan was a middling team that had won just one Serie A title in nearly two decades. That all changed when Berlusconi bought the team, pumping a lot of money into the club to make things better. Things quickly turned around for Milan with the club winning the 1987-88 Serie A title.

Under Berlusconi, Milan would go on to win a total of eight Serie A titles to go along with seven Supercoppa Italiana titles. After just over three decades of ownership, Berlusconi sold Milan to Rossoneri Sport Luxembourg for €740 million. The Berlusconi era came with a total of 29 trophies, five of which were European Cups/Champions League titles.

Biggest La Liga Win

Winning any Serie A game can prove to be difficult, but to absolutely decimate another professional team in the top league is incredibly rare. In the rare occasions that it does happen, though, it’s certainly noteworthy. One of the most talked about Serie A games of the 21st century came when Milan walloped Torino 7-0 in league play in May 2021.

Theo Hernandez opened up the scoring for Milan in the 19th minute while Franck Kessie made it a 2-0 game on a penalty kick. While that’s a comfortable lead to have at the half, Milan was nowhere close to done. Hernandez added a second goal while Brahim Diaz got on the board in the 50th minute. From the 67th minute to the 79th minute, Ante Rebic scored a hat trick, giving Milan a 7-0 lead. Surprisingly, the club held off on scoring in the final 11 minutes, but it was still the largest league win in club history.

Claiming the Champions League

AC Milan has won the European Cup/UEFA Champions League several times throughout the years, dating back to the club’s first win in 1962-63. After the mid-1990s, though, Champions League titles were harder to come by, which made the run in the 2006-07 season special, especially when you consider the club finished third in the Serie A standings and had to take on Red Star Belgrade in the qualifying round.

Milan snuck past Lille and AEK Athens in the group stage standings, then needed extra time to defeat Celtic in the round of 16. After a huge 2-0 win in the second leg against Bayern Munich, Milan used a 3-0 second-leg victory to get past Manchester United. In the final against Liverpool, Pippo Inzaghi scored just before the half, then added a goal in the 82nd minute to give AC Milan a 2-0 lead. Dirk Kuijt netted a goal for Liverpool in the 89th minute, but it was too late as Milan claimed the Champions League title.

Inter 0-6 Milan

Of course, beating your biggest rival is always going to be a great moment, but when you absolutely demolish them, it’s even sweeter. In the 30th matchday of Serie A play, AC Milan locked horns with Inter. While Milan didn’t really have a chance to reach the Champions League or win Serie A, they were still able to knock out their biggest rival in record fashion.

Gianni Comandini scored in the third minute of the match, then added a second goal just 16 minutes later. The scoring then resumed in the second half with Federico Giunti scoring in the 53rd minute, followed by two Andriy Shevchenko goals. Serginho capped things off in the 81st minute, giving Milan the 6-0 victory.

AC Milan has one of the most storied histories in Italian football with a long list of accomplishments that includes Serie A titles, Champions League trophies, and much more. However, there have been some low points for the club, with these five moments perhaps being the worst for AC Milan fans.

Europa League Bouncing

The Champions League is where the best UEFA teams compete, while the Europa League is the secondary tournament. Those who have expectations of the Champions League like Milan could see it as a bit of a consolation, but the players still take the tournament very seriously. In the 2018-19 edition of the tournament, Milan still had high hopes during their financial rebound (more on that later).

During the group stage in the round of 32, however, Milan didn’t play their best. In their six matches, AC Milan won just three games while drawing one and losing two. Milan finished tied for second with Olympiacos but had a goal differential of just +3. It knocked them out of the tournament and set a low point for the modern era of AC Milan football.

The 1990-91 Euro Ban

The 1990-91 European Cup was an interesting one for AC Milan. The club was the only team to qualify for the second round after Ajax’s spot was vacated. Milan was the two-time defending champion, and they were expected to compete once again. Milan ran into Club Brugge in the round of 16 but only won 1-0 on aggregate over two legs. In the quarterfinal, Milan squared off against Marseille.

The two clubs drew in the first leg 1-1 with Ruud Gullit scoring for Milan and Jean-Pierre Papin scoring for Marseille, with both goals coming in the first half. During the second leg, Marseille was up 1-0 when half of the floodlights in Stade Velodrome went out. When the power came back on after 15 minutes, Milan refused to come back on the pitch. This earned Marseille a 3-0 awarded victory with Milan receiving a one-year ban from European competition.

Financial Troubles Lead to Near-Ban

While the European Cup resulted in a finalized ban, there was a proposed ban many years later that the club nearly suffered. Between the end of 2015 and the summer of 2017, AC Milan reported a net loss of €146 million. This was well in excess of the €25 million allowed by UEFA’s Financial Fair Play Regulations. The result was a €12 million penalty and a proposed one-year ban from European competition.

The club was able to get the ban lifted, thankfully, but it opened a lot of eyes to just how much Milan was spending in hopes of bolstering the roster. Milan had until June 2021 to break even, which they did. The process took away some of the star power that Milan was able to afford previously, but they rebounded quickly after the penalties came down and ended up winning the 2021-22 Serie A title.

2005 Champions League Final

Some of the most heartbreaking moments in sports come when a team or individual has a massive lead, only to see it dwindle away and result in a loss. It hurts even more when there’s a massive prize on the line. That was the case for AC Milan at the 2005 UEFA Champions League final. The club had gotten through the group stage rather easily and then defeated Manchester United and rival Inter Milan handily.

After sneaking by PSV Eindhoven in the semis, they took on Liverpool for the title. Milan struck in the first minute with a Paolo Maldini goal, then Hernan Crespo added two more in the final six minutes of the first half. It looked like the match was all but over, but Liverpool stormed back hard. Steven Gerrard, Vladimir Smicer, and Xabi Alonso all scored in a seven-minute span to force extra time. Neither team scored, sending it to penalties where Liverpool won 3-2.

Totonero Scandal

There have been a handful of big match-fixing scandals throughout Serie A history, and one of the big ones came in the form of Totonero 1980. The scandal included Milan and a handful of other teams from both the top league and Serie B. Milan and Lazio took the biggest punishments with both clubs relegated to Serie B while other clubs were penalized points and some individuals were banned or even imprisoned.

Milan didn’t waste much time getting back into Serie A, however. In their one season with Serie B, the club finished with 50 points in 38 games. Along with Genoa and Cesena, they made the move back up. The long road back to the top of Serie A concluded with a league title in the 1987-88 season that saw them finish three points ahead of Napoli.

Without a doubt, Juventus has been one of the most successful clubs in all of Italian football. Despite all of the money that has come in thanks to all of the title-winning seasons, there has been plenty of money lost due to poor signings. 

Whether they’re injury related, performance-related, or players simply having issues with management, these are the five worst signings in Juventus history. Before we start the list, some of the players who just missed the cut include Jean-Alain Boumsong, Jonathan Zebina, Amauri, and Marcelo Salas.

Jorge Martinez

Uruguay native Jorge Martinez kicks off the list, with the midfielder showing signs of becoming a star while with the Montevideo Wanderers. He made his professional debut in 2000, spending seven years with the senior squad before moving to Catania. After another three years, 86 matches, and 22 goals, Martinez made his way to Juventus. The club paid €12 million for his services on a four-year contract.

Things got off to a terrible start as Martinez suffered an injury in his first match. It didn’t seem that he was too affected performance-wise upon his return, but it was shortlived as Martinez continued suffering injuries. When front-office changes were made, Juventus was looking for a fresh start and loaned out Martinez to several teams over the course of six years. All in all, Martinez made just 14 league appearances for Juventus.

Nicklas Bendtner

Nicklas Bendtner is a tall forward from Denmark who impressed so much as a youth in his home country that he landed a deal with Arsenal at 17. Bendtner went on to make his senior squad debut in 2005 with Arsenal, spending nearly a decade with the club while being loaned out to Birmingham City and Sunderland. The third club to acquire him via loan was Juventus, who spent €6 million for the remainder of the 2012-13 season with an option to make the move permanent.

Unfortunately, that move would not be made permanent for multiple reasons. Bendtner suffered an injury that limited him to just nine matches and he was held scoreless for all of them. Bendtner was also arrested for driving drunk, making things more complicated. Another injury came in the form of a fractured wrist, and the experiment ended with Bendtner returning to Arsenal.

Diego

We head back to South America for the next player on the list, this time to Brazil where Diego Ribas da Cunha hails from. Simply known as Diego around the world, the midfielder was a tremendous player for Santos after making his debut in the early 2000s. Diego went on to spend time with Porto and Werder Bremen, making over 130 combined appearances for the clubs. In 2009, Diego and Juventus reached a five-year agreement worth €24.5 million.

The type of production that he had with Bremen didn’t translate into success with Juventus, however. The club played a much different style, and Diego almost immediately had problems with management. Because Juventus couldn’t use him the way that they wanted to, Diego played in just 33 matches. He scored five goals during that time and was sent to VfL Wolfsburg in 2010.

Christian Poulsen

The second Dane on the list, Christian Poulsen was a midfielder who found a lot of success early in his career, including winning the Danish Superliga, DFB Ligapokal, and Copa del Rey. Poulsen started his professional career in 1997 with Holbaek, then made his way to Copenhagen, Schalke 04, and Sevilla. Juventus then paid a €9.75 million transfer fee to obtain Poulsen, giving him a four-year contract.

However, Poulsen wouldn’t last nearly that long. He made just 48 league appearances and lasted until 2010. Juventus wasn’t able to claim any major titles during the Poulsen era, and he remains a testament to the overspending that the club did during the early 2010s. Poulsen finished with one goal during his Juventus career before being sent to Liverpool. He eventually played for Evian and Ajax before finishing his career with a return to Copenhagen.

Felipe Melo

We conclude the list with another Brazilian player, meaning that none of the worst signings were actually from Italy. The top spot belongs to Felipe Melo, another midfielder who ended up being a massive overpay after showing signs of potential superstardom. Melo began his career with Flamengo in 2001, then had stints with several clubs over the subsequent years including Gremio, Racing Santander, and Almeria.

Melo was part of Fiorentina from 2008 to 2009, with Juventus coughing up €25 million to acquire him. While things looked good in the first match, they quickly went sour after Melo started fighting with his teammates and his level of play took a nosedive. Melo made less than 60 league appearances with Juventus and was sent to Galatasaray on a loan that would end up being permanent.

Inter Milan has had countless matches throughout its history that have had a lot of importance. Between league matches, international competition, and more, some Inter victories have meant more than others. Let’s take a look at five classic matches that every Inter fan should know about.

Ending the Drought

Heading into the 2020-21 Serie A season, Juventus had been unstoppable for nearly a decade. The club had won the league title in nine consecutive years after Inter had enjoyed a long streak of its own during the 2000s. Many were wondering when A. Juventus would be knocked off, and B. When Inter would get back into the title picture.

Things got off to a shaky start to the season as Inter won just two of its first four games, but things would turn around quickly. After the fourth matchday, Inter would lose just two more times the rest of the season. On the 34th matchday, Inter lined up against Crotone with a chance to win Serie A and end the Juventus reign at the top. It took until the 69th minute, but Christian Eriksen finally got Inter on the board while Achraf Hakimi added a second goal to give Inter the 2-0 victory and the Serie A title.

First Champions League Title

Inter had won the European Cup in back-to-back years during the 1960s but had no other title victories throughout the league’s history, even as it changed to the UEFA Champions League in the early 1990s. Heading into the 2009-10 season, Inter still hadn’t won the Champions League, but fortunes would change quickly. Placed into a group with Barcelona, Rubin Kazan, and Dynamo Kyiv, Inter claimed second place to advance.

Inter got past Chelsea in the round of 16, then CSKA Moscow and Barcelona in the quarterfinals and semifinals, respectively. In the final, Inter took on Bayern Munich in Madrid, Spain. Inter struck first when Diego Milito scored in the 35th minute. Milito then added a second goal in the 70th to give Inter the 2-0 victory and its first Champions League title.

Thrashing of Milan

In the Derby della Madonnina, there aren’t many blowouts (at least not since the earliest parts of the 20th century). That’s why when one team wins by more than two goals, it becomes global news. During the 2009-10 Serie A season, Inter faced off against Milan twice in the rivalry. Inter won the second match by a 2-0 mark, but the first match was even more memorable as Inter blanked Milan 4-0 in front of their own supporters.

Thiago Motta got the scoring started in the 30th minute when he scored on a fine pass from Diego Milito. Milito then added a goal of his own six minutes later on a penalty to make it 2-0. Milito got back on the assist side for the third goal of the first half with Maicon netting one in the 45th minute. In the second half, Inter scored once more with Dejan Stankovic putting in a goal in the 67th minute while Milan got shut out.

Tiebreaker For the Title

Things were much, much different in the days before Inter joined Serie A as part of the top league in Italy. During the early 20th century, Inter was part of Prima Categoria and won its first major league title in the 1909-10 season. That year, there were 16 matches on the schedule, with Inter winning 12 of them while drawing one and losing three. Pro Vercelli had the same record, forcing a tie-breaker match.

The match proved to be a very interesting one that would never happen today. Pro Vercelli had already scheduled an exhibition match for that day in 1910 (April 24) and Inter didn’t want to postpone. Pro Vercelli had to send their fourth squad to the match, which was comprised of 15-year-old boys. Inter would end up winning the title thanks to a wild 10-3 victory over the young lads.

Coppa Italia Resurgence

The Coppa Italia tournament started in 1922, but Inter had won the tourney just once heading into the late 1970s (1938-39). Inter would get back into the contender picture starting with the 1977-78 edition of the tournament and stay there for decades. Inter was placed into a group with Ascoli, Atalanta, Cremonese, and Como. Inter won three of its four matches, drawing in the other.

Inter then won the second-round group, defeating Fiorentina, Torino, and Monza. In the final, Inter took on Napoli, and it didn’t look good at the start as Maurizio Restelli netted a sixth-minute goal in Rome. Alessandro Altobelli equalized things in the 18th minute. Scoring halted until the 89th minute. That’s when Graziano Bini scored the historic goal to give Inter its second Coppa Italia title.

Inter Milan has had one of the best histories of any football club throughout Europe, and especially in Italy. Inter has trophies from all of the major tournaments, but which moments stand out as the best in club history for fans? Here are our picks for the top five moments.

The First Supercoppa

The Supercoppa Italia was introduced in 1988 with the winner of Serie A taking on the Coppa Italia winner to determine the true top Italian football team. In the first contest, Milan got to take on Sampdoria, winning the title 3-1. The following year, Inter would get its shot against Sampdoria, doing so in San Siro. While attendance was low for the competition, it was still a moment of triumph for Inter.

Enrico Cucchi scored the lone goal of the first half while Aldo Serena netted one of his own in the 86th minute. The match ended with that 2-0 mark, giving the club its first of many Supercoppa Italiana titles. 

The 30th Win

Inter has had a lot of successful seasons in Serie A, but none as successful as the 2006-07 campaign. The season opened up with a 3-2 win over Fiorentina, and was then met with a mixture of draws and wins over the following six matches. Then, Inter went on a winning streak that lasted from October 25, 2006, to February 28, 2007. Even then, the club went 31 weeks without a loss to begin the season.

The only loss of the season came on the 32nd matchday against Roma. Inter went on to win its next five matches before drawing 1-1 with Atalanta in the penultimate week. It was a bit frustrating as Inter was looking to become the first Serie A team with 30 wins in a season, but there was one more shot. On the final matchday, Inter defeated Torino 3-0 to give the club its record 30th win against just seven draws and one loss. They finished 22 points ahead of second-place Roma in the standings, too.

Securing the Back-to-Back

Prior to the 2010 Champions League final (more on that in just a moment), Inter Milan had to go several decades without winning one of football’s biggest trophies. The two previous times that Inter won the Champions League, it was known as the European Cup, and they won it in back-to-back years. The first came in 1964 with Inter defeating Real Madrid 3-1 inside Prater Stadium in Vienna.

The second one was even sweeter, though. The 1965 final took place in San Siro, with 89,000 on hand to support Inter against Portuguese club Benfica. Just before halftime, Jair scored a goal that made it 1-0 Inter, and it was a score that would hold up for the rest of the match. In front of their fans, Inter hoisted the European Cup to mark a brief period of dominance that wouldn’t return for nearly a half-century.

Treble in 2010

Inter had a fantastic season in 2009-10, despite the fact things got started off with a draw against Bari. Throughout the year, Inter would go on long undefeated streaks, which included more than three months throughout the La Liga season. Inter lost on March 27, 2010, against Roma 2-1, but finished with six wins and a draw to close out the season. The club needed at least one point in the final week of the season to clinch the title, and did so with a 1-0 victory against Siena.

The good times didn’t end there as Inter also had a solid run through the Coppa Italia. After getting through Livorno, Juventus, and Fiorentina, Inter took on Roma in the Coppa Italia final. Diego Milito scored in the 39th minute for Inter, and that would be the only goal that the club needed, giving Inter the second part of the treble. As for the third part…

Return to Champions League Glory

The third piece of the puzzle was the UEFA Champions League, which is something that Inter hadn’t won since 1965 when it was known as the European Cup. Despite the club’s success in the 2009-10 season, not many were sure if they had what it took to win the Champions League, especially after a tough draw in the group stage.

After finishing in second place behind Barcelona and only having two wins, Inter turned things on in the knockout round. The club got past Chelsea, CSKA Moscow, and Barcelona to reach the final. There, they took on Bayern Munich and capped off the amazing run and season. Diego Milito scored in the 35th minute to give Inter the 1-0 lead, then added his second goal in the 70th minute. That was all that Inter needed, giving them their first Champions League title in 45 years.

Real Madrid has been one of the most successful football clubs in all of Europe, and as a result, there is no shortage of memorable moments for fans. However, we’re going to narrow it down to just a handful, with these five being the best moments in club history. From momentous goals to legendary signings, these moments change the club forever.

The Shush

El Clasico always means more for Real Madrid fans, and on October 13, 1999, it meant everything. Coming into the match, Real Madrid hadn’t beaten Barcelona in nearly three full years. In fact, in their previous matchup, Barcelona defeated Real 3-0. Things would change that day in Camp Nou, and even though Real Madrid didn’t win the match, the draw would be something that turned the tide of the rivalry.

Raul scored first in the 26th minute, putting Real Madrid ahead 1-0. However, Rivaldo answered back for Barca just two minutes later. In the second half, Luis Figo scored in the 49th minute, and Real Madrid tried to crawl back for an equalizer. It took until the 86th minute, but in front of a rowdy Camp Nou, Raul netted his second of the game to tie things up. He rushed around the field silencing the crowd, and Real Madrid would go on to win their next match against Barca 3-0.

The Signing of Ronaldo

When you’re one of the richest clubs in football you’re able to get some of the best players. However, it’s not every day that you get one of the greatest players in the sport’s history. Portuguese forward Cristiano Ronaldo will go down in history as one of the all-time legends, and he made his professional debut with Sporting CP in 2002. The following year, he became a superstar as a member of Manchester United and stayed with the club for six years.

Real Madrid already knew just how good Ronaldo was, and didn’t scoff at paying a record €94 million transfer fee worth €11 million per year. It was certainly a slam-dunk move, and it thankfully didn’t end up being an overpay. Thanks to Ronaldo, Real Madrid won La Liga and the Copa del Rey twice, as well as the UEFA Champions League in four out of five years. He also won the Ballon d’Or four times.

La Decima

When the UEFA Champions League was formed as the European Cup during the mid-1950s, it was always going to be a big deal when a club won the league for the 10th time. Real Madrid dominated during the 1950s while adding a couple more during the 1960s. After struggling in the 1970s and 1980s, Real Madrid returned to form to work toward La Decima.

Thanks to winning the title in 1998, 2000, and 2002, Real Madrid had many shots at finally getting that 10th title. However, it took until 2014 for the club to get back to the final. After getting through the group stage of the 2013-14 UEFA Champions League, the club got through a German gauntlet of Schalke 04, Borussia Dortmund, and Bayern Munich. While the 110th-minute goal to make it 2-1 was a massive moment, everyone knew it was over when Marcelo netted one in the 118th to make it 3-1. The icing on the cake was Ronaldo’s 118th-minute penalty kick, clinching La Decima with a 4-1 extra-time win.

Zidane’s Champions League Winner

We already mentioned the 2002 Champions League win briefly, but it certainly needs to be talked about as one of the best moments in Real Madrid history. The club came in with high expectations and easily got through the group that had Roma, Lokomotiv Moscow, and Anderlecht. Real then advanced through the second group stage, again with ease, before knocking out Bayern Munich and archrival Barca to reach the final.

Raul scored in the eighth minute to give Real the 1-0 lead, but Bayer Leverkusen knotted things up just six minutes later. Right before halftime, Zinedine Zidane scored one of the greatest goals in football history, completely deflating Bayer. Neither team scored afterward, and Real clinched its ninth Champions League title.

The 11th Goal

We couldn’t finish the list without mentioning the biggest beatdown in El Clasico’s history. Though it goes way back in the past, it’s hard to let your archrival down after a 10-goal margin. In the 1943 Copa del Generalisimo semifinals, Real and Barca went head-to-head at Estadio Chamartin.

It took until the 89th minute for Barcelona to score its lone goal. As for Real, Pruden knotted a hattrick in the first half, Chus Alonso scored two, while Antonio Alsua and Pascual Botella added one. Sabino Barinaga was the biggest star of the game, scoring four times en route to Real’s 11-1 victory.

There have been some amazing moments throughout the history of Inter Milan football. After all, the club is the only one in Italy that has never dropped below Serie A. That doesn’t mean that everything has been perfect for the club over the years, though. Let’s take a look at Inter Milan’s long history, highlighting the five worst moments for the club’s fans.

The Worst Match in Club History

No matter how good a club is or how many titles it has won, there are going to be some very bad losses deep in team history. In the case of Inter Milan, that loss came back in 1961 during the Serie A season when matched up against Juventus. In that season, Inter finished in third place in the league, just one point behind AC Milan and five points behind Juventus.

Juventus was able to maintain its top spot thanks to the drubbing it gave Inter on June 9, 1961. Omar Sivori scored a hat trick between the 11th and 17th minutes, giving Juventus a 3-0 lead at the half. He then scored another hat trick in the second half while Francesco Riefolo, Bruno Nicole, and Bruno Mora all scored once each. In the end, Juventus won the match 9-1.

Near Relegation

As we mentioned, Inter Milan is the only club in Italian football to never drop below the Serie A level of play. That doesn’t mean that the club hasn’t come awfully close to being relegated a handful of times. The closest that the club got was in the fateful 1993-94 season. Inter Milan got off to a fine enough start, losing just one of its first 10 matches while winning five. However, things turned south in a hurry.

In the last 14 matches of the season, Inter won just twice with a 1-0 victory over Udinese and 4-1 victory over Lecce. The club needed at least a draw to avoid relegation in the penultimate matchday, doing so against AC Roma 2-2. Inter finished with 11 wins, nine draws, and 14 losses, good enough for 31 points. That put them one ahead of Placenza, who was relegated to Serie B.

The 1997 UEFA Cup Final

Now known as the UEFA Europa League, the UEFA Cup was one of the most prestigious tournaments throughout the continent. During the 1990s, Inter was able to secure the UEFA Cup championship three times with wins in 1991, 1994, and 1998. However, there was a loss in between that hurt badly. That came in the 1996-97 UEFA Cup season, with Inter being one of the favorites to win.

Inter Milan didn’t struggle much throughout the tournament, getting by Guingamp in the first round before defeating Grazer AK, Boavista, Anderlecht, and AS Monaco to get to the finals. Back then, the final was two legs, and Inter lost the first leg 1-0. In the second match, facing an aggregate loss, Zamorano scored an 84th-minute goal to send the final to penalty kicks. Zamorano proceeded to miss his first shot while Schalke 04 scored on each of theirs, giving them the UEFA Cup.

Luigi Simoni’s Exit

The entirety of the 1990s resulted in little success for Inter, and they had to watch their rivals win trophies on both a national and continental level. That would be understandable if Inter hadn’t been trying to win, but the club spent more money than just about any other club in football. In fact, Inter set the record for the highest-ever transfer fee twice toward the end of the decade when they acquired Ronaldo and then Christian Vieri.

The end result was zero Serie A titles throughout the decade, and one of the most heartbreaking moments for fans. Massimo Moratti took over the club in 1995, and two years later hired Luigi Simoni to lead the team as manager. However, Simoni was given a short leash, and despite being beloved by fans while winning a UEFA Cup, was relieved of his duties in November 1998. Simoni went on to have seven more managing stints before retiring in 2006.

The Calciopoli Scandal

Pretty much any professional club in Italy could call the Calciopoli scandal one of their worst moments. That’s certainly the case for Inter Milan, who was implicated in the scandal that saw clubs working with officials to fix matches. However, despite being named, it was really only Juventus that saw major consequences while Inter got away without much damage done to the club.

Former Juventus president Giovanni Cobolli Gigli commented about the situation, saying that Inter was just as guilty. “Everyone has forgotten this matter, if Inter had been in the sports trial with Juventus, and had been accused, as happened only years later, of ‘serious sporting offense,’ it would have been a different story,” he said. “Someone hid the file, someone powerful. Why try to hide something like that…I didn’t understand.”