Inter Milan's hopes of reaching the knockout stages of the Champions League were dealt a huge blow as Real Madrid claimed a 2-0 victory at the San Siro.
Arturo Vidal was shown two yellow cards by referee Anthony Taylor after Inter's penalty claims were waved away.
Eden Hazard converted an early spot kick for Real, with Achraf Hakimi scoring an own goal.
Antonio Conte's side are rooted to the bottom of Group B with just two points from four games.
The win for Zinedine Zidane's men moves the thirteen-time European champions up into second place in the group, one point behind leaders Borussia Monchengladbach.
Gladbach cruised to a 4-0 victory over Shakhtar Donetsk in the earlier kick off, scoring three first-half goals to boost their hopes of qualifying top of the group.
Monchengladbach 4-0 Shakhtar Donetsk
Olympiakos 0-1 Manchester City
Atletico Madrid 0-0 Lokomotiv Moscow
Bayern Munich 3-1 RB Salzburg
Inter Milan 0-2 Real Madrid
Marseille 0-2 FC Porto
Ajax 3-1 FC Midtjylland
Liverpool 0-2 Atalanta