Sergio Gomez was sent off and Riyad Mahrez missed a penalty as Manchester City were held to a goalless draw by Copenhagen in the Champions League.
City knew a win would seal their place in the round of 16 with two games to spare, but they endured a frustrating Tuesday evening at Parken.
Rodri had a goal disallowed for a handball by Riyad Mahrez, who then had a spot-kick saved by Kamil Grabara before Gomez was dismissed for a professional foul in an eventful first half.
Erling Haaland was an unused substitute as City's six-game winning run came to a halt and they lost their 100 per cent Group G record, but they remain on the brink of qualifying for the next stage.
Rodri rifled a thunderous long-range strike into the top-left corner in the 11th minute, but referee Artur Dias ruled the goal out for a Mahrez handball after a being instructed to look at the pitch-side monitor.
Mahrez wasted a chance to make amends from the spot after Nicolai Boilesen was adjudged to have handled following another VAR check, but Grabara dived to his left to deny the winger midway through the first half.
There was another big blow for City on the half-hour mark, when Dias was once again summoned to the touchline and the busy Portuguese official deemed that Gomez had pulled Hakon Haraldsson down to deny him a goalscoring opportunity.
Pep Guardiola's side were dominating possession despite being a man down and Grabara punched away a Kevin De Bruyne strike early in the second half.
Isak Johannesson came agonisingly close to Victor Kristiansen's teasing cross from the left at the other end as Copenhagen scented a famous victory.
Grabara produced more heroics by diving to his right and palming away Joao Cancelo's drive as neither side could fashion a winner.
What does it mean? Free-scoring City fire a rare blank
The Premier League champions had scored 24 goals in their six-match winning streak, but they failed to find the back of the net for the first time since a goalless draw with Atletico Madrid back in April.
Copenhagen lacked the quality to punish Gomez and Mahrez, with Guardiola leaving the prolific Haaland on the bench ahead of a clash with Liverpool at the weekend, while Phil Foden and Bernardo Silva were only introduced late on.
Group leaders City will qualify if Sevilla fail to beat second-placed Borussia Dortmund later on Wednesday, while Copenhagen are in third place without a goal in their four matches.
Grab comes up clutch
It was an evening to remember for Copenhagen goalkeeper Grabara, who read Mahrez's intentions to keep his side on level terms.
He was commanding throughout, showing great reflexes as he made four saves to keep City at bay.
Misery for Mahrez
Mahrez will want to forget his trip to the Danish capital in a hurry
The Algeria international's handball denied Rodri a stunning opening goal and his tame penalty was telegraphed, his second miss from the spot in the last three he has taken for City. Mahrez was then hauled off after Gomez saw red, Ruben Dias replacing him.
Key Opta Facts
- Manchester City became the first team to miss a penalty and have a player sent off in the first half of a Champions League game since Arsenal against Bayern Munich in February 2014.
- Copenhagen have failed to score in each of their past seven matches against English teams in all competitions since a 2-1 defeat away to Manchester City in February 2009.
- City have only lost two of their past 27 group stage games in the Champions League (W20 D5), with this game the third occasion in this run the Citizens saw red but avoided defeat (also versus Atalanta, in both October and November 2019).
- Riyad Mahrez has missed two of his last three penalties in all competitions for City, after missing just one of his first 10 for the club.
What's next?
City travel to Anfield to face Liverpool in the Premier League on Sunday, while Copenhagen end the week with a trip to Brondby.
