Milan edged their way through to the Europa League group stage with a remarkable 9-8 penalty shoot-out victory over Rio Ave, following on from a dramatic 2-2 draw between the teams on Thursday.

Without Zlatan Ibrahimovic, who tested positive for coronavirus last week, Milan put in a lacklustre showing in their final qualifying match and looked to be heading out after Gelson Dala put Rio Ave ahead early in extra time.

However, Hakan Calhanoglu restored parity from the spot with the final kick of the game after Toni Borevkovic's handball, with the defender sent off after receiving a second yellow card.

Alexis Saelemaekers' effort six minutes into the second half had put Milan in front earlier in the contest, though Francisco Geraldes' thunderous strike cancelled out their lead.

During an incredible shoot-out that saw both goalkeepers miss their attempts, Gianluigi Donnarumma eventually came up with the save to send Milan through.

Brahim Diaz's introduction following a dire first half sparked Milan into life, the substitute winnig the corner which led to Saelemaekers drilling in a low finish to break the deadlock.

Tarantini's block prevented Calhanoglu from making it 2-0 and Rio Ave made their luck count – Lucas Piazon laying it back for substitute Geraldes to lash the ball home.

Picking up where they left off, Rio Ave took the lead early in the first period of extra time when Gelson dispatched a low finish across Donnarumma.

The home team looked to have kept Milan at bay through to seal a famous triumph, but their luck turned in the final minute when Borevkovic was adjudged to have handled in the area, allowing Calhanoglu to convert from 12 yards.

That was far from the end of the drama, though. After 14 superb penalties, Lorenzo Colombo's skied effort started a bizarre series of events, with Nelson Monte hitting the post before both goalkeepers sliced over.

Geraldes struck the woodwork after Ismael Bennacer's attempt was saved, but the pressure finally told on Rio Ave when Donnarumma kept out Aderllan Santos' spot-kick.

2003 - #ACMilan have won a game in European competitions at the Penalty Shootout for the first time since the Champions League Final in 2003, against Juventus at the Old Trafford. Deliverance.#RioAveMilan pic.twitter.com/EsSgxYiP3C
— OptaPaolo (@OptaPaolo) October 1, 2020

What does it mean? Milan get the job done… just about

It has been a fantastic start to the season for Stefano Pioli's side, but they were incredibly wasteful in this game, managing just three attempts on target from 24 shots. They progressed, however, via penalties, their first shoot-out success in a European match since 2003.

Donnarumma stands tall to finally end shoot-out

After letting a tame penalty from Ivo Pinto squirm in, Milan's goalkeeper took an awful spot-kick of his own. However, he regained his composure to make an excellent stop and secure the visitors' progression.

A poor day at the office for Castillejo

Milan's attack was way off the pace in the first half, with Samu Castillejo the player to pay. He made way at half-time having had just 20 touches and attempted only eight passes, with an accuracy of 37.5 per cent. In a match full of poor displays, Castillejo's was the standout for the wrong reasons.

What's next?

Milan host newly promoted Spezia in Serie A on Sunday, while Rio Ave are in domestic action against Famalicao.