TIME MACHINE: AC MILAN v BOLOGNA | OneFootball

The 2025/26 Serie A season resumes for the third matchday, following the first international break. AC Milan will face Bologna for the first time since the defeat in the Coppa Italia final on May 14th. The match will take place at San Siro, and in the build up to the game, let's relive one of our previous encounters with the Felsinei. Let's rewind to the 1999/00 season. Alberto Zaccheroni was manager for the Rossoneri, who wore the Tricolore proudly on their shirts, after winning the Rossoneri's 16th Scudetto in May, in Perugia.

On September 25, 1999, more than 50,000 spectators filled San Siro for the fourth matchday of the league. In their previous three games, the reigning Italian champions had one win (against Perugia) and two draws (against Lecce and Bari). Zaccheroni rolled out his 3-4-3 formation, featuring a star-studded front three of Leonardo, Bierhoff, and Weah. The big surprise was in defense, where he went with an untested back three of Maldini, Ayala, and N'Gotty. Weah opened the scoring in the 8th minute, slotting it in from close range after an excellent header by Bierhoff. The press in attack paid off - after regaining posession, Leonardo broke away making it 2-0 in the 44th minute, putting AC Milan ahead before the break.

We controlled the game in the second half, and just ten minutes in, Oliver Bierhoff got on the scoresheet too, with a penalty won by Leonardo who was brought down by Pagliuca. Maurizio Ganz came off the bench to secure the win with a classic Inzaghi-style goal, pouncing on the ball after Leonardo's long-range effort was parried away to the left. It was a convincing 4-0 victory for AC Milan. The season would ultimately end with a third-place finish, behind Lazio and Juventus, but with the league's best attack and Andriy Shevchenko as the top scorer with 24 goals in his debut Serie A season.

Subscribe to the AC Milan WhatsApp channel!