Raheem Sterling struck early for the Premier League champions in Milan but Gabriel Jesus missed a penalty before Mario Pasalic levelled in a dramatic second half that saw City reduced to 10 men.
Goalkeeper Claudio Bravo, a half-time replacement for the injured Ederson, was controversially sent off 10 minutes from time for bringing down Josip Ilicic.
Kyle Walker had to play in goal for the closing minutes but City held on for a draw that still maintains their healthy position at the top of Group C.
With qualification the prize for a victory, manager Pep Guardiola had intended to leave nothing to chance by fielding a strong side. Only Sergio Aguero of the probable starters for Sunday’s clash at Liverpool was rested. By the end, however, he may have been counting the cost with the crucial figure of Ederson joining a lengthy injury list.
Son Heung-min bounced back from his weekend devastation as he scored two goals in Tottenham’s impressive 4-0 Champions League win at Red Star Belgrade.
Son was visibly distraught after his tackle led to a horrific injury to Everton’s Andre Gomes on Sunday and he was a doubt to make the trip to Serbia as a result.
But he put it all behind him in Belgrade with a double in four second-half minutes to take his tally to nine Champions League goals in 2019 and five in four games this season.
His brace added to Giovani Lo Celso’s first goal for the club and a late Christian Eriksen strike, as Spurs finally won away for the first time since May 8 – the famous night against Ajax in Amsterdam.
The victory, in a stadium where Liverpool were beaten last season, puts the Premier League side in the driving seat to join Group B leaders Bayern Munich in the knockout stages.
Unai Emery remained defiant when asked about the possibility of being replaced by Jose Mourinho after seeing his Arsenal side let a lead slip for the fourth game in a row as they were pegged back by Vitoria Guimaraes of Portugal in the Europa League.
Asked about the Mourinho links and the fan criticism, Emery simply replied: “I am the coach.”