City had plenty of opportunities to extend their lead before the break but a combination of poor finishing and inspired goalkeeping from Moroccan goalkeeper Yassine Bounou kept the lead at a single goal.
Al Hilal offered several reminders of their threat on the break but City had even more chances, with Jeremy Doku volleying straight at Bounou – who moments later reacted superbly again to keep out a Bernardo effort.
City punished
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The question as to whether City would live to regret not converting those chances was answered within a minute of the resumption.
Former City fullback Joao Cancelo’s low cross was parried out by Ederson, Brazilian Malcolm pounced but saw his shot blocked by Ruben Dias, only for the ball to loop to Leonardo to head home the equaliser for 1-1.
Six minutes later and City’s high defensive line was exposed by a long ball from Cancelo, which Malcolm raced on to, showing power and pace as he broke away before coolly slotting past Ederson.
The Saudi fans in the crowd went wild while City manager Pep Guardiola responded immediately with a triple substitution, introducing midfielder Rodri and defenders Nathan Ake and Manuel Akanji.
That brought some much-needed stability to a shaky backline but City needed improvement at the other end too and it came, albeit in scruffy circumstances.
The Al Hilal defence were unable to deal with a Bernardo corner and Erling Haaland pounced to steer home the loose ball and make it 2-2.
City piled on the pressure as they looked for the winner but, yet again, Bounou proved their nemesis as he denied Akanji and Ruben Dias and even when he was beaten by Haaland, substitute Ali Lajami produced a magnificent goal-line clearance.
Guardiola took off Haaland and introduced Egyptian forward Omar Marmoush as the game went into extra time.
But for all City’s depth, Al Hilal had a deep well of spirit to draw upon and regained the lead just four minutes into the opening period, when Kalidou Koulibaly rose superbly to meet a Ruben Neves corner with a brilliantly angled header.
City responded with a goal of real quality when Rayan Cherki’s brilliantly floated ball towards the back post was poked home masterfully by Phil Foden, at full stretch and from the tightest of angles.
But incredibly, Al Hilal responded again to restore their lead – Sergej Milinkovic-Savic’s header was saved by Ederson but Marcos Leonardo followed in to bundle the ball over the line.
As the celebrating Al Hilal fans poured out of the stadium, the Brazilian striker let his emotions pour out.
“I’ve had a difficult time in the last two months. My mother spent 70 days in the ICU,” he said.
“Today she’s fine, thank God. When I scored those two goals, I thought of her. She was able to watch the match.”
City skipper Bernardo Silva said his team had paid the price for being unable to deal with Al Hilal’s counter-attacking.
“We scored three and could’ve scored five, six. It was all about controlling when we lost the ball, controlling the transitions, don’t let them run, and they ran way too many times,” he said.
“With one, two passes there was always a feeling of danger coming from them. When we allow teams to run like this, we always suffer a lot and today was the case,” he said.
**– Agence France-Presse**