The match finished 2-2 at full-time but at the end of an eventful extra-time Marcos Leonardo grabbed the winner and pulled off one of the biggest wins in Middle Eastern football history.

The Saudi club advance to the quarter-finals where they will face Brazilian club Fluminense, ensuring a non-European team will reach the last four.

Pep Guardiola's City had come into the game brimming with confidence after a 5-2 dismantling of Juventus in their final group game but they were upset by an Al Hilal side full of verve and determination under new Italian coach Simone Inzaghi.

City took the lead in the ninth minute and it was in controversial fashion. Rayan Ait-Nouri burst into the box and his cross took two deflections before landing at the feet of Bernardo Silva who slotted home.

But the Al Hilal players insisted that Ait-Nouri had controlled the ball with his arm and their protests intensified after the stadium screen showed the incident.

But Venezuelan referee Jesus Valenzuela was unmoved by the players who delayed the re-start and urged him to check the monitor and the goal stood.

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.

Both Savinho and Ilkay Gundogan were denied at close-range by Bounou who then did well to tip a Josko Gvardiol header over the bar.

Al Hilal offered several reminders of their threat on the break but City even more chances with Jeremy Doku volleying straight at Bounou who moments later reacted superbly again to keep out a Bernardo effort.

City punished

The question as to whether City would live to regret not converting those chances was answered within a minute of the resumption.

Former City full-back Joao Cancelo's low cross was parried out by Ederson, Malcolm pounced but saw his shot blocked by Ruben Dias only for the ball to loop to Marcos Leonardo to head home the equaliser.

Six minutes later and the City's high defensive line was exposed by a long ball from Cancelo which Brazilian Malcolm raced on to and he showed power and pace as he broke away before coolly slotting past Ederson.

The Saudi fans in the crowd went wild while Pep Guardiola responded immediately with a triple substitution with midfielder Rodri and defenders Nathan Ake and Manuel Akanji introduced.

That brought some much needed stability to a shaky back line but City needed improvement at the other end too and it came, albeit in it scruffy circumstances.

The Al Hilal defence were unable to deal with a Bernardo corner and Erling Haaland pounced to steer home the lose 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 just four minutes into the opening period Al Hilal regained the lead 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.

K. Koulibaly

Achievements