From 1988 through 1994, Milan was unstoppable. They not only won a lot of trophies, but they did so in a gallant style that fundamentally changed the game, especially in their own country. Arrigo Sacchi revolutionised football by introducing the pressing game, and as a result, he oversaw Italian football's most successful era in Europe. When he moved on to the national team, his successor Fabio Capello carried on the tradition. The club included one of the most impressive defences ever built, a hardworking midfield, and front-line flair players.

Coach: Arrigo Sacchi & Fabio Capello

Trophies: 3 Serie A titles (1991–92, 1992–93, 1993–94), 3 European Cups/Champions League (1988–89, 1989–90, 1993–94), 4 Supercoppa Italiana (1988, 1992, 1993, 1994), 3 European Super Cups (1989, 1990, 1994), 2 Intercontinental Cups (1989, 1990)

Star Players: Ruud Gullit, Marco Van Basten, Frank Rijkaard, Franco Baresi, Paolo Maldini, Alessandro Costacurta, Zvonimir Boban, Savicevic, Marcel Desailly, Demetrio Albertini.

Milan won their tenth league title in 1979, but the following year, with Gianni Rivera's retirement, the team began to collapse. The club was embroiled in the 1980 Totonero affair and was relegated to Serie B for the first time in its existence as a result of the punishment. The controversy revolved around a betting syndicate that paid players and officials to rig matches. Milan was promoted to Serie A for the first time after winning the 1980–81 Serie B title but were demoted a year later after finishing third-worst in the 1981–82 season. Milan won Serie B for the second time in three seasons in 1983, allowing them to return to Serie A.

Then two men appeared, and everything changed. President Silvio Berlusconi had the money and the determination, but Rossoneri needed someone in charge. He found his man in Arrigo Sacchi, who made an impression when his Parma team came to San Siro in the Coppa Italia and won, then repeated the feat in 1987 over two legs. He also signed Ruud Gullit, Marco van Basten, and Frank Rijkaard, all of whom are Dutch internationals. The Dutch trio provided an attacking boost to the team, complementing Paolo Maldini, Franco Baresi, Alessandro Costacurta, and Roberto Donadoni, the club's Italian internationals.

In the 1987–88 season, Milan won its first Scudetto in nine years under Sacchi's leadership. Milan's semi-final victory over Real Madrid CF in the 1988/89 European Cup was a historic moment for the club.  At home, Madrid was thought to be invincible, and Milan was anticipated to sit back and take it in the first leg at the Santiago Bernabéu. Sacchi, on the other hand, had other ideas. His team grabbed control and were unfortunate to be held to a 1-1 draw. It doesn't matter. They triumphed 5-0 in the return leg in Milan, with Ancelotti scoring the game's first goal. The club defeated Romanian club Steaua București 4–0 in the final to win its first European Cup in two decades.

With a sleek 4-4-2 system that included zonal marking (then unheard of in Italy), a high defensive line, and springing the offside trap, they made rival teams exceedingly uncomfortable. Sacchi’s workouts were well-known for their rigour and intensity. He was recognised for doing a lot of work without a ball to improve player positioning, and it paid off. Milan won the European Cup again a year later, defeating Benfica 1–0, and was the only team to win back-to-back European Cups until Real Madrid did so in 2017. In the Italian press, the Milan team of 1989–90 was dubbed the "Immortals."

But after a trophy-less season in 1991/92, Sacchi departed, replaced by Fabio Capello. It was just the shot in the arm Milan needed to get back on track. As their love affair with the Champions League continued, they won another league title, as well as numerous domestic honours and a narrow defeat in the final against Marseille. They came together for one more dance in 1993/94, summoning all of their class and experience and adopting a more defensive strategy to beat Juventus by three points.

In 1994, Milan conceded only 15 goals and reached the Champions League final for the second time, despite the fact that few people gave them a chance against Barcelona's Dream Team. Barcelona were favourites to win their second European Cup/UEFA Champions League in three years after winning La Liga for the fourth consecutive season. Milan's preparations for the final were in disarray. Marco van Basten, the club's legendary striker, was still out with a long-term injury, while Gianluigi Lentini, the £13 million youthful prodigy, was also hurt. Franco Baresi, the captain and sweeper, was suspended, as was defender Alessandro Costacurta. Coach Fabio Capello was forced to leave Florin Răducioiu, Jean-Pierre Papin, and Brian Laudrup out due to UEFA regulations at the time, which prohibited teams from fielding a maximum of three non-nationals.

Milan took control early on and were rewarded when Dejan Savicevic dashed down the right-wing and passed to Daniele Massaro, who tapped the ball into an empty net. After a solo run down the left flank by Roberto Donadoni, Massaro scored his second shortly before halftime to make it 2–0. Savicevic scored the third goal in the 47th minute, capitalising on a defensive blunder by Miguel Angel Nadal to lob goalkeeper Andoni Zubizarreta. After Savicevic had struck a post and the Barcelona defence had failed to clear, Milan midfielder Marcel Desailly overcame the offside trap eight minutes later to make it 4–0, which was the final score.

They turned up the heat one last time in Athens, destroying Barça with a stunning display of aggressive football and lifting the trophy that had been synonymous with them throughout that golden era. The revolution of the Rossoneri was accomplished. In the 1994 Final, they stunned doubters by defeating a superb Barcelona squad 4-0. Maldini would go on to play for Milan for another 15 years, becoming a legend in the process. Italian football hasn’t been the same since.