Franck Kessie’s penalty proved enough, but Milan only scraped past 10-man Red Star Belgrade on away goals thanks to a stunning Gianluigi Donnarumma save.
The first leg of this Europa League Round of 32 ended 2-2 in Belgrade, with the Serbians twice battling back to equalise, even after a red card. Milan Rodic was therefore suspended, with Aleksandar katai and Veljko Nikolic injured, while the Rossoneri missed Ismael Bennacer and Mario Mandzukic.
The deadlock was broken in contentious circumstances, because Rade Krunic had shinned his shot horribly and it went practically sideways, striking Marko Gobeljic on the arm. Nonetheless, VAR and the referee decided it was worthy of a penalty, converted coolly by Franck Kessie. He dedicated the goal to Willy Ta Bi, the Atalanta youth player who replaced him in Bergamo and died this week from cancer at 21.
Ben Nabouhane had the ball in the net on 19 minutes, but it was only after Pankov had handled in order to provide the assist.
It was all Red Star after that penalty, as Ben Nabouhane saw his free kick bounce off the crossbar with Gianluigi Donnarumma beaten, then he drilled in the deserved equaliser from a tricky angle with his left foot after running onto the Ivanic through ball.
There was a huge Borjan save on Diogo Dalot, sticking out a leg to parry when the ball was rolled across from the right to find the defender totally unmarked.
Kanga blasted not far wide from 30 metres out and Krunic was inches away from another penalty, brought down right on the edge of the area.
Zlatan Ibrahimovic and Ante Rebic came on for the second half, but they should’ve combined for a goal, the Swede knocking down a Hakan Calhanoglu cross only for Rebic to prod wide from six yards.
Ivanic saw his strike deflected to flash across the face of goal and Ben Nabouhane had penalty appeals rejected for a Samu Castillejo nudge.
Gianluigi Donnarumma on his 22nd birthday made one of the saves of his career, somehow clawing the ball off the line when Sanogo had volleyed from a couple of yards, then the rebound was somehow fired off target by Gobeljic.
It went from bad to worse for Gobeljic moments later, as he received a second yellow card for a foul on Calhanoglu and, just like the first leg, Red Star went down to 10 men.
Alexis Saelemaekers had the ball in the net, but only after Ibrahimovic was offside on the assist. Yet again, Red Star continued to threaten even after the red card, Katai hitting the side-netting from a very promising position.
While Rebic managed to waste two counter-attacks, Red Star pinned Milan back to the very last second of the tie, going out on away goals.
Milan 1-1 Red Star Belgrade (3-3 agg)
Kessie pen 9 (M), Ben Nabouhane 24 (RS)
Milan: G Donnarumma; Calabria (Theo Hernandez 66), Tomori, Romagnoli, Dalot; Meite, Kessie; Castillejo (Saelemaekers 66), Krunic (Rebic 46), Calhanoglu; Leao (Ibrahimovic 46)
Red Star Belgrade: Borjan; Pankov, Degenek, Sanogo; Gajic, Kanga, S Srnic (Petrovic 46), Gobeljic; Ben Nabouhane (Falco 69), Ivanic (Nikolic 84); Falcinelli (Pavkov 72)
Ref: Manzano (ESP)
Sent off: Gobeljic 70 (RS)