Milan twice fumbled the lead in Belgrade and were pegged back by 10-man Red Star in stoppages, but a 2-2 away draw is still a good first leg result.
This was the first leg of the Europa League Round of 32, reaching the knockout stages of the tournament that the Rossoneri had begun in the preliminary rounds. Zlatan Ibrahimovic and Franck Kessie were rested ahead of Sunday’s Serie A showdown with Inter, so Mario Mandzukic got his first start with lifelong Crvena Zvezda fan Rade Krunic.
It was an aggressive Milan start, as Samu Castillejo had his goal ruled offside and Ante Rebic forced a save at the near post.
Theo Hernandez thought he had opened the scoring moments later when the goalkeeper fumbled a Pierre Kalulu cross and Mandzukic nodded it down for the full-back. However, that too was disallowed for Mandzukic’s handling offence.
Krunic stung the goalkeeper’s gloves from distance, but Gianluigi Donnarumma had to rush off his line to clear from Mirko Ivanic.
Rebic also fired over the bar from a smart Krunic assist, while Donnarumma flew to palm another Ivanic strike round the post.
Ismael Bennacer limped off with a muscular problem, making way for Sandro Tonali.
Milan did get a stroke of luck soon after, though, as Castillejo’s roll across seemed predictable, yet Radovan Pankov came sliding in to accidentally prod it slowly past the goalkeeper into his own net.
Ben Nabouhane tested Donnarumma at the near post straight after the restart, but Alessio Romagnoli had his arm very outstretched when connecting with Diego Falcinelli’s flick, so a penalty was inevitable. Guelor Kanga converted with a well-taken spot-kick, although Donnarumma was very close to getting it.
Milunovic was booked for a body-check on Krunic and will be suspended for the second leg. Just as Milan were under pressure and struggling to get out of their half, they were awarded a soft penalty on the counter, as Theo Hernandez went down under minimal pressure from Pankov. Theo converted the spot-kick himself, celebrating with a theatrical bow.
Castillejo forced another save and Rodic received his second yellow card for stopping a Pierre Kalulu counter-attack.
Soualiho Meite had a free header from a set play, but Borjan flew to fingertip it over the bar.
Milan seemed content to keep hold of the 2-1 result against 10 men, but it was a mistake, because Red Star Belgrade equalised with the looping Milan Pavkov header from a corner that left Donnarumma stranded.
Red Star Belgrade 2-2 Milan
Pankov og 42 (M), Kanga pen 52 (B), Theo Hernandez pen 61 (M), Pavkov 93 (B)
Red Star Belgrade: Borjan; Milunovic, Pankov, Degenek; Gobeljic (Gajic 74), Kanga, N Petrovic (Sanogo 81), Rodic; Ben Nabouhane (Falco 61), Ivanic (Bakayoko 81); Falcinelli (Pavkov 81)
Milan: G Donnarumma; Kalulu, Tomori, Romagnoli, Theo Hernandez (Dalot 77); Meite, Bennacer (Tonali 39); Castillejo, Krunic, Rebic (Leao 46); Mandzukic (Calhanoglu 82)
Ref: Sidiropoulos (GRE)
Sent off: Rodic 77 (B)