Rio Ave 2-2 AC Milan (AC Milan win 9-8 on penalties)

In one of the most impressive showings by a Portuguese sides on the continental stage, Rio Ave went toe to toe with AC Milan, and were within seconds of pulling off a stunning upset, but fell just short of getting the job done, defeated 9-8 in a breathtaking penalty shoot-out.

In the buildup to the game, it was regularly said that a Rio Ave victory would have been one of the greatest achievements in Portuguese football history - and the Vila do Conde side more than held their own against their prestigious Italian opponents.

Having already secured an impressive penalty shootout victory over Turkish giants Besiktas in the previous round, Rio Ave had already pulled off a minor upset, but they knew they would have to go one step further if they wanted to get a result again AC Milan.

And they did almost everything right. In a first half that was balanced, Rio Ave defended well and looked comfortable on the ball, but AC Milan did take the lead just after half time with a powerful low shot from Saelemaekers.

Rio Ave were not disheartened though, and kept working right until the end, continuing to play their game and show good quality on the ball. And it wasn’t too log before Geraldes fired the club level, smashing the ball into the back of the net in the 71st minute.

And that was how the score remained as the full time whistle blew, ensuring extra time would be required to separate the two sides.

And it was Rio Ave that struck first, with Gelson Dala’s low and accurate strike finding the bottom corner just 30 seconds after extra time kicked off - and Rio Ave were suddenly just half an hour away from an almighty upset.

They started to sit deeper as they looked to protect their lead, and for 29 minutes did so with very few problems. However, in the 120th minute of the game, a lapse of concentration and a moment of desperation from Borevkovic saw the centreback handle the ball in the box, and AC Milan were awarded a very late penalty. Calhanoglu converted with the very last kick of the game, and Rio Ave had to settle for penalties.

The shootout was legendary. Of the first 14 penalties taken, every single one was converted, including a cheeky chip from Filipe Augusto - and it was 7-7 as tension built.

With Rio Ave taking second, they kept holding their nerve to stay level with AC Milan even in sudden death, and their chance to win it came when Colombo, taking the 15th penalty of the shootout, hit his effort over the bar. Nelson Monte knew that if he scored, Rio Ave would complete the upset and advance, but his effort struck one post and then cannoned off the other in the most unfortunate of circumstances.

Braga soon had another chance when AC Milan’s goalkeeper Donnarumma struck his effort well over the bar, but Braga’s own shot-stopper, under pressure, made the same mistake, and his penalty also sailed over the bar.

Rio Ave then had a third opporunity to qualify for the Europa League group stage when Kieszek made up for his miss by saving Bennacer’s shot, but Chico Geraldes’ accurate effort hit the post and came out. It just wasn’t Rio Ave’s night.

AC Milan, on the brink of elimination four times, finally got the job done when Aderllan Santos’ spot-kick was parried out by Donnarumma, and the Italian outfit’s players were visibly ecstatic as the final whistle blew. Rio Ave pushed them all the way, but the David and Goliath story did not have a happy ending.