Manchester City traveled to the San Siro looking to seal a spot in the Champions League round of 16. However, they failed rather spectacularly in their attempts, as they were held to a 1-1 draw by Atalanta.
Raheem Sterling opened the scoring for Pep Guardiola's side, capping off a wonderful move with a sweet strike into the bottom corner.
Gabriel Jesus missed a golden opportunity to get on the scoresheet himself as he sent a penalty well wide of the target on the stroke of halftime.
Atalanta then emerged from the break with a spring in their step and took the attack to City. Soon enough, they found themselves level thanks to Mario Pasalic's bullet header.
Despite finding themselves a man to the good following Claudio Bravo's sending off, Atalanta could not press home their advantage, with both the teams sharing the spoils at the final whistle.
Here we take a look at three of the biggest talking points from an entertaining encounter at the San Siro:
#1 VAR gets it right, twice in 2 minutes!
VAR has copped plenty of criticism of late, especially for the way it's been implemented in the Premier League. However, tonight's contest showed just how useful the technology can be when used in the right manner.
With five minutes to go until half-time, referee Aliaksei Kulbakov awarded Manchester City a penalty after Raheem Sterling was brought down by Rafael Toloi. However, replays suggested that the contact was initiated just outside the box which meant the decision was overturned upon review.
From the subsequent free-kick, City were denied a penalty for a handball shout against Josip Ilicic. However, after taking a closer look at the incident on the pitch-side monitor, the referee was forced to reverse his decision once again and point to the spot.
Although there remain plenty of concerns regarding the technology and its shortcomings, it is clear that VAR, if used properly, can be quite a handy tool.
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#2 Red card, penalty miss and a whole lot of drama
A game that began in ever-so-dull fashion sparked into life after 40 minutes. Gabriel Jesus was in the spotlight for the wrong reasons, sending his spot-kick well wide of the target when presented with the opportunity to put the game to bed.
City were then dealt a second blow when star goalkeeper Ederson had to be withdrawn at half-time due to injury. That clearly sparked Atalanta into action as the Italian side equalised soon after the restart through Mario Pasalic.
To rub salt into City's wounds, Claudio Bravo, who had replaced Ederson at half-time, was then shown a red after bringing down a goal-bound Josip Ilicic.
This meant Kyle Walker had to fill in between the sticks for the final 10 minutes of the game. Walker was tested almost immediately from a free-kick but managed to keep the ball out, albeit in unconvincing fashion.
Much to City's relief, Atalanta failed to register any meaningful attacks during the time Walker was in goal and had to remain content with a point.
#3 Atalanta pick up first-ever Champions League point
Atalanta began their Champions League campaign with plenty of optimism; however, all that was washed away within 10 minutes of their debut in the competition.
Losses to Dinamo Zagreb, Shakhtar Donetsk and Manchester City meant they became the first Italian team to lose their first three games of the tournament.
A defeat tonight would have also made them the first side since Otelul Galati in 2011-12 to drop their first four Champions League matches.
However, they managed to avoid that embarrassing milestone by holding the defending Premier League champions to a 1-1 draw.
In the process, Atalanta also secured their first-ever Champions League point, although it could have been so much more had they been a little more clinical in front of goal.
Mario Pasalic's 49th-minute strike canceled out Raheem Sterling's opener but despite putting City under enormous amounts of pressure in the second period, the Italians failed to break through a second time.