AC Milan managed to qualify for the group stage of the Europa League on Thursday evening with the greatest possible difficulty. I Rossoneri still took the lead against Rio Ave, but ultimately needed a penalty kick in the last minute of extra time to force a 2-2 draw. In the subsequent penalty series, no less than 24 penalties were taken before goalkeeper Gianluigi Donnarumma could make the decisive save.

Milan could not rely on the injured Zlatan Ibrahimovic and Ante Rebic against the number five of last season in the Liga NOS and with an attack consisting of Samu Castillejo, Daniel Maldini and Alexis Saelemaekers had i Rossoneri struggling to make a fist offensively. It took until five minutes after half-time for Milan to get its first good chance and then it was immediately hit by Saelemaekers. The Belgian got the ball after a corner turned off on the edge of the box and his slider was too powerful for Pawel Kieszek.

Milan seemed to be on roses with that, but about twenty minutes before the end, it was suddenly level again with a bang through the bottom of the bar by Francisco Geraldes. In the remainder of the official playing time, no more goals were scored, after which it was hit in the first minute of extra time when Dala Gelson got the ball through Franck Kessié and Gianluigi left Donnarumma without a chance in the far corner.

The Italians therefore had to chase and in the remainder of the extension got a number of opportunities to straighten things out. A free kick by Ismaël Bennacer, however, was picked from under the crossbar by Kieszek and Theo Hernández also had no luck five minutes before the end of the game when he shot a rebound right at the goalkeeper. In minute 120, however, Milan was still in the right place when Toni Borevkovic touched the ball in the box by hand. The defender had to come in with a second yellow card and Hakan Calhanoglu brought his team alongside at the last minute.

In the decisive penalty shootout series it remained extremely exciting. The first fourteen penalty takers were all accurate before Lorenzo Colombo shot his attempt hard. Rio Ave had the chance to take the win, but Nelson Monte saw his penalty carom out of the goal via two posts. After a hit by Rafael Leão, Donnarumma thought to turn the bet of Ivo Pinto, but the ball ended up in the goal via the goalkeeper. The two keepers then shot their bets over the goal, after which they started again. Bennacer was not accurate this time, however, and Geraldes also hit the post. After a second penalty from Simon Kjaer, it was Donnarumma’s save on Aderlan Santos’ penalty kick that decided the game.