AC Milan ensured their place in the Europa League group stage after beating Rio Ave 9-8 on penalties in the playoff round with the game locked at 2-2 after extra time at a rain sodden Estadio dos Arcos in Portugal on Thursday evening.
A second half strike from Alexis Saelemaekers would give the Rossoneri the lead, before Francisco Geraldes brought the Rioavistas level with a quarter of the game remaining.
Then a well taken goal by Gelson gave the hosts the advantage less than a minute into extra time, but a penalty from Hakan Calhanoglu in 122nd minute sent the game into a penalty shootout.
It was the Rossoneri who started the contest as the better of the two teams as they dictated the tempo of the game with the lions share of possession, but with the exception of two long range free kicks that went well wide they created little in the way of clear cut opportunities.
With the hosts happy to keep nine men behind the ball the first half was rapidly becoming a drab affair as Milan toiled away to no avail against a green and white wall of Rioavistas.
It would take nearly half an hour for the game to see its first shot on target when, despite the Rossoneri’s dominance, the host’s Carlos Mane fired a tame long range effort into the hands of Gianluigi Donnarumma.
When the opening stanza eventually came to an end Stefano Pioli’s men trudged back to the dressing room visibly frustrated with a game that was producing very little in the way of entertainment.
The break sparked the Rossoneri into life and it took them just over five minutes of the second half to open the scoring when the Rioavistas failed to clear their lines from a corner. The ball found its way to Saelemaekers, who was all alone on the edge of the box, and he drove a low shot into the bottom corner with Pawel Kieszek rooted to the spot in Rio Ave goal.
However, the Rossoneri’s goal forced the hosts into action and they would be the better team for remainder of the game. With the visitors now firmly on the back foot they looked nervous and their advantaged was extinguished with only a quarter of the game remaining.
A well worked move by the Rioavistas saw the ball make its way to the feet of Geraldes, who hammered his shot past Donnarumma to bring the hosts level.
With neither team able to find a winning goal before the 90 minutes was up the tie headed into an unwanted period of extra time that would provide the a goal after less than 60 seconds. A defensive mix up in the Rossoneri back line allowed Gelson a clear run at goal and he beat Donnarumma with ease to give Rio Ave the lead.
As the game headed to its conclusion the Rossoneri were handed a lifeline when they were awarded a penalty in 122nd minute for handball and Calhanoglu stepped up to send the game into a penalty shootout.
Both teams converted eight of their first 12 penalties in a seemingly never ending shootout before Simon Kjaer gave the Rossoneri the advantage and Donnarumma saved Jambor’s effort to give Milan the victory.
Milan will now have turn their attentions back to Serie A action on Sunday evening when they host newly promoted Spezia at the Stadio San Siro. .