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Update AC Milan reached the Europa League group stage after a nervy 9-8 penalty shootout win
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AC Milan reached the Europa League group stage after a nervy 9-8 penalty shootout win over Portuguese club Rio Ave on Thursday, having netted a fortunate last-gasp equalizer in extra time.

Milan trailed 2-1 in extra time until Toni Borevkovic gave away a penalty in the 121st minute with a careless handball, allowing Hakan Calhanoglu to level from the spot. Rio Ave then had three chances to win the penalty shootout but missed each time, before Milan goalkeeper Gianluigi Donnarumma made the decisive save to send his team through.

The shootout featured 24 penalties in total, with both goalkeepers sending their efforts over the bar.

Tottenham had no such troubles as Harry Kane scored his first hat trick of the season in a 7-2 win over Maccabi Haifa.

However, last year’s quarterfinalist Basel and German club Wolfsburg were both eliminated.

Rio Ave also looked set to spring an upset after Gelson gave the Portuguese club the lead in extra time. However, Borevkovic inexplicably downed a high ball into the area with his hand to give away a penalty with just seconds left — getting his second yellow card in the process.

In the shootout, Nelson Monte first had a chance to win it for Rio Ave with the score at 7-7, but his penalty hit the left post and then rolled across the goalline before hitting the other post and going out.

After Donnarumma sent his penalty over the bar at 8-8, his counterpart Pawel Kieszek did the same. And when Chico Geraldes was given a third chance to win it for the Portuguese side, his effort hit the right post.

Tottenham's win came exactly a year to the day after losing 7-2 to Bayern Munich at home in the Champions League group stage

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