Milan rode their luck to the very end of an extraordinary Europa League play-off with Rio Ave, snatching an equaliser with the last kick of extra time and winning an epic penalty shoot-out.
This was the final hurdle towards the Europa League group phase, after getting the better of Shamrock Rovers and Bodo/Glimt, but the Portuguese side had eliminated Besiktas in the last round and were not to be underestimated. Zlatan Ibrahimovic had COVID-19, Ante Rebic was suspended, so Daniel Maldini got his first competitive start for Milan, following in the footsteps of father Paolo and grandfather Cesare.
Theo Hernandez drilled a free kick routine wide and then saw a shot charged down accidentally by one of his teammates, while Gianluigi Donnarumma gathered a swerving Carlos Mane attempt from distance.
Calhanoglu’s intelligent through ball for Theo Hernandez was crucially intercepted by Aderllan Santos.
Milan were utterly toothless and Samu Castillejo repeatedly gave the ball away, so he was replaced by Brahim Diaz for the second half.
It made an immediate difference, as the substitute surged forward to complete a give and go with Saelemaekers, his deflected finish forcing a corner. From that set play, it came to the edge of the area for Saelemaekers to hit it low and hard into the near bottom corner.
Theo Hernandez also sprinted through the middle to exchange passes with Saelemaekers, but lost his footing at the crucial moment.
Tarantini’s diving header on a corner flashed wide, while Rafael Leao came on, immediately won a free kick in the D that Calhanoglu saw deflected wide.
Rio Ave’s substitutes made an impression too, as Francisco Geraldes was barely on for five minutes when he ran forward, exchanged passes with Piazon and rifled a ferocious left-foot strike into the top corner.
The momentum and confidence were suddenly with Rio Ave, but Milan picked up in the final minutes, Calhanoglu’s volley deflected wide and a Davide Calabria rocket off target.
In stoppages, the hosts had a huge chance to win it, as Jambor’s volley was charged down and on the rebound Santos prodded inches wide of the upright. There was no decider and it went to extra time.
Within seconds of the restart, Milan were caught cold and went 2-1 down. Gelson won it back in midfield, got lucky with the ricochet off Franck Kessie’s shin and reacted quickly to fire an angled drive into the far bottom corner.
Leao had a promising run into the box only to trip over his own feet, Piazon had another strike charged down, while Ismael Bennacer’s free kick was fingertipped over the bar and Matteo Gabbia’s header off target from the resulting corner.
Theo Hernandez’s powerful effort stung the goalkeeper’s gloves after a corner, but Rio Ave defended stoutly and Milan couldn’t find the inspiration to break through.
However, as the final minute ticked down, Borevkovic was penalised for a completely avoidable handling offence in the area. It was his second yellow card, the referee pointed to the spot and Calhanoglu converted a penalty to equalise with the last kick of the game.
It went to a shoot-out and that too was utterly bizarre. Everyone converted, it went to sudden death, even then they couldn’t be separated. When Lorenzo Colombo fired over, so did Monte. When Donnarumma missed the target, so did his counterpart Kieszek. Ismael Bennacer’s was saved, but Gerlades at his second go round hit the upright.
Eventually, Santos saw his attempt saved by Donnarumma to send Milan into the Europa League group phase after 24 spot-kicks.
Rio Ave 2-2 Milan (aet, 10-11 pens)
Saelemaekers 51 (M), Francisco Geraldes 72 (R), Gelson 91 (R), Calhanoglu pen 122 (M)
Bennacer (M, goal), Geraldes (R, goal), Kjaer (M, goal), Santos (R, goal), Theo Hernandez (M, goal), Jambor (R, goal), Brahim Diaz (M, goal), Piazon (R, goal), Calhanoglu (M, goal), Filipe Augusto (R, goal), Calabria (M, goal), Gelson (R, goal), Tonali (M, goal), Gabrielzinho (R, goal), Colombo (M, miss), Monte (R, miss), Leao (M, goal), Ivo Pinto (R, goal), Donnarumma (M, miss), Kieszek (R, miss), Bennacer (M, saved), Geraldes (R, miss), Kjaer (M, goal), Santos (R, saved)
Rio Ave: Kieszek; Ivo Pinto, Santos, Borevkovic, Nelson Monte; Filipe Augusto, Tarantini (Jambor 75); Piazon, Diego Lopes (Francisco Geraldes 66), Carlos Mane (Gabrielzinho 109); Moreira (Gelson 85)
Milan: G Donnarumma; Calabria, Kjaer, Gabbia, Theo Hernandez; Bennacer, Kessie (Tonali 106), Castillejo (Brahim Diaz 46), Calhanoglu, Saelemaekers (Colombo 95); Maldini (Leao 67)
Ref: Gil Manzano (ESP)
Sent off: Borevkovic 120 (R)
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