AC Milan couldn’t have made life any more difficult for themselves, but they found a way to make it past Rio Ave and into the Europa League group stages.
Alexis Saelemaekers opened the scoring for the Rossoneri in the second half, but goals from Geraldes in normal time and Gelson Dala early in extra time had Milan trailing until the 120th minute.
Drama then struck as a penalty was awarded for handball which Hakan Calhanoglu despatched, and then an absolutely incredible penalty shootout occurred in which Rio Ave spurned three winning kicks as Milan fought back to win 9-8.
Stefano Pioli went into the game knowing he could not call upon Ante Rebic, Zlatan Ibrahimovic, Alessio Romagnoli, Mateo Musacchio, Leo Duarte and Andrea Conti, and the main selection surprise was that Daniel Maldini got the nod up front over Lorenzo Colombo.
The opening exchanges were frantic and typical of two sides trying to impose their own style on the game, with Milan pressing high and Rio Ave trying to play through the middle, the highlight of the opening 10 minutes being a Simon Kjaer shot from his own half that was hit with venom but ended up at least 10 yards wide.
The Rossoneri fired their first meaningful effort on goal in the 12th minute through a well-worked free-kick routine that had clearly come straight from the training ground. After two touches the ball was rolled back towards Theo Hernandez, though the Frenchman fizzed his effort wide of the right post from the best part of 30 yards out.
Milan were clearly fancying their chances from distance as Hakan Calhanoglu then decided to take aim from 40 yards, but he wasn’t able to recreate one of his famous knuckleball free-kicks, instead skewing the attempt wide.
The game slipped into the same cycle in which the home side sat deep and deployed a low block, Pioli’s side couldn’t quite cut through them, they lost the ball and won it back fairly quickly before once again battling against a deep defensive line.
Both sides were struggling to generate any real quality in terms of their passing let alone shooting, but Gianluigi Donnarumma was called into action for the first time when Carlos Mane cut in from the left wing and curled an effort towards the far post that the No.99 was easily able to step across and catch given his huge frame.
Ultimately, the referee would blow for half time without either side having a clear cut opportunity, and for Milan the main threat had come from Theo Hernandez’s marauding runs.
It was understandable then that Pioli made a change at the break, with the disappointing Castillejo making way for Brahim Diaz.
Early in the second half Aderllan went into the book for Rio Ave for what was a very smart tactical foul as he hauled down Maldini, who was in a position where it was easy to slide Calhanoglu through one-on-one.
The difference with Brahim on the field was almost instant as Milan began knocking on the door. The Spaniard saw a shot blocked inside the area after a neat feed from Saelemaekers with what was a last-ditch slide.
However, it was from the resulting corner that Milan took the leader. An outswinging ball from the right found its way to Saelemaekers on the edge of the box, and he took a touch to steady himself before firing inside the near post with a measured finish from his right foot.
GOOOOOAAAAALLLLLL! ALEXIS! pic.twitter.com/tTkOfy7RDS
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Tarantino had a big chance to equalise for the home side just before the hour mark as he stooped down to head a cross towards goal, but it somehow went comfortably wide of the far post despite the fact the forward was unmarked.
Pioli made his second change of the evening midway through the second half as Daniel Maldini made way for Rafael Leao.
Leao put his stamp on the game straight away, receiving the ball with his back to goal before spinning and embarking on a jinking run to the edge of the box where he was cynically tripped. From the resulting free-kick, Calhanoglu saw his shot deflected narrowly wide of the top corner.
Ultimately though Milan would be made to pay for their missed opportunity as Rio Ave levelled. A move down Milan’s right side ended with Geraldes hitting a first time shot past Donnarumma following a perfect cut-back, making the score 1-1.
Milan came close to retaking the lead six minutes from times when a long throw found its way to Calhanoglu on the edge of the box, whose reflex shot whizzed wide. From the corner that followed Calabria did a similar thing but from 10 yards further out, and this time without a deflection.
Rio Ave had the best chance to win it inside 90 minutes as Santos shot inches wide from the edge of the box after a ball ricocheted to him, but the game would end up going to extra-time.
With the first attack of extra time, Rio Ave took the lead for the first time in the match. Gelson Dala was able to run through on goal after flicking the ball against Kessie’s legs, though his finish into the far corner gave Donnarumma no chance.
Pioli tried another roll of the dice from the substitute’s bench five minutes into extra time, with Colombo coming on for Saelemaekers.
Kieszek was forced into a save on the stroke of half time in extra time, tipping Bennacer’s free-kick over the bar, before Gabbia headed wide from the corner that came after.
Kessie made way during the interval, with Sandro Tonali coming on in Milan’s final change.
The Rossoneri began to make inroads, and Theo Hernandez was found with an excellent through ball by Tonali before his cross needed a near post intervention, while from the resulting corner Theo saw an effort from the edge of the box parried away.
Absolute disaster struck for the hosts in the final minute of extra time. A desperate long ball was flicked over the top and in behind, where Borevkovic inexplicably put an arm out and handled the ball, conceding a penalty and receiving a second yellow card for his worries.
Calhanoglu stepped up and despatched the spot kick with venom to ironically send the tie to a penalty shootout, with the players on the floor after an extra 30 minutes in their legs they probably didn’t need.
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Bennacer took the first penalty for Milan and found the bottom right corner perfectly, but Geraldes responded by sending Donnarumma the wrong way. Kjaer then strode forward and beat Kieszek with a powerful effort, yet Santos covered confidently to make it 2-2 after four spot kicks.
Theo Hernandez was next and he did just as good a job as his two team-mates by finding the inside side netting, though yet again Rio Ave hit back through Jambor. Brahim Diaz couldn’t have hit his penalty any sweeter into the top left corner to make it 4-3, but Piazon made it 4-4 with a calm effort.
Calhanoglu repeated his exploits from the dying seconds by firing another incredible penalty into the bottom corner, however captain Augusto ensured it would go to sudden death with a perfectly executed panenka.
Calabria went next and again the left side of the goal was kind to Milan as he tucked the ball away, but the shootout continued as Gelson Dala scored. Tonali went next and did the exact same as Calabria; Gabriel responded. 7-7.
Colombo went next and blasted his attempt over the bar, yet somehow Milan stayed in it as Monte’s penalty hit both posts and rolled away.
Leao then took on responsibility and confidently rocketed the ball home, and Donnarumma knows he should have saved Pinto’s effort as the ball hit his arm and went over the line. He will have felt even worse seconds later as he skied his penalty, however Kieszek did the exact same.
And so back to the start we went, but this time Bennacer could not score with Kieszek saving well low to his left. Geraldes curled his effort on to the post, and we went on. Kjaer thumped home down the middle to make it 9-8, and Donnarumma came up with a decisive save when it mattered to book Milan’s place in the Europa League group stages.