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.