Some early heroics from Manuel Neuer and a red card to opposite number Wojciech Szczesny ultimately doomed Arsenal to a 2-0 home defeat against Bayern Munich.
The London side exerted early pressure against the defending European champions but never recovered from an early penalty miss from Mesut Ozil.
And despite Bayern missing their own penalty in the first half, the Bavarians took advantage of their one-man advantage with goals to Toni Kroos and Thomas Muller sealing the tie.
While Bayern drew the first save, with Wojciech Szczesny tipping a Kroos effort over the bar, it was Arsenal who dominated in the opening salvo.
Yet a solid performance from Neuer’s between the sticks kept the scorelines level, with three crucial saves in less than ten minutes.
The turning point came in the eighth minute when Wilshere’s deft turn and pass sent Ozil through on goal.
A clever cut inside the box coaxed Jerome Boateng into a foul, forcing referee Nicola Rizzoli to point to the spot.
It was a chance for Ozil to vanquish his poor recent form, yet his casual and jolted run-up saw Neuer keep out his weak effort.
Ozil’s penalty style has been around too long for fans to be surprised – when he slots them it looks effortless, when he misses it looks lazy.
Yet it was the second penalty miss from the German international in the Champions League this season.
At the time of his last miss, against Marseille in November, Arsene Wenger bizarrely announced that it was “good news for England”.
It wasn’t good news for Arsenal this time round, however, as the team, and particularly Ozil, reclined into their shell.
From there Bayern found their rhythm and began bossing the tie.
Philipp Lahm, so often the anchor in Pep Guardiola’s 4-1-4-1 formation this season, had slotted back into his natural right back position and was marauding the left side of Arsenal’s defence time and time again.
Flamini and Mertesacker put their bodies on the line to block shots from Alaba and Robben, while Koscielny was crucially winning most of his aerial duels.
A brilliant play from Yaya Sanogo, so often overlooked as a replacement for the benched Olivier Giroud, saw Alex Oxlaide-Chamberlain bear down on goal, only for Neuer once again to save the day.
Yet it was a flowing Bayern attack that threatened to demolish Arsenal’s promising start in the 37th minute.
Robben cut in from the right, played a one-two with Toni Kroos and deftly picked the return ball from the air before Sczcesny crashed into his legs.
The Polish keeper was shown red and Bayern had their own chance from the spot.
Alaba stepped up for penalty duties yet saw his effort crash back off the post after beating substitute keeper Lukasz Fabianski.
It was an astonishing end to a remarkable opening 45 minutes.
A change for Bayern at half-time saw Rafinha on for Boateng, with Javi Martinez pushing back in defence and Lahm moving into the holding midfield spot.
A relentless charge a goal began and it wasn’t long before the Bavarians took the lead.
A simple one-two between Lahm and Kroos pulled Arsenal players out of position in the 54th minute, giving Kroos a moment’s space to rocket a fierce shot past Fabianski.
It was Bayern’s 100th goal of the campaign and it wasn’t to be their last of the night.
A string of close calls, threatened to crush Arsenal’s valiant defensive display, yet they stayed strong for most of the second half.
Thomas Muller’s introduction for a largely ineffective Mario Mandzukic in the 64th minute proved an inspired change from Pep Guardiola.
The German forward almost got on the end of a Rafinha cross and had a strong penalty shout turned down before slotting Bayern’s crucial second away goal.
Lahm sent a ball into Arsenal’s box on 88 minutes and with the defence at sea Muller had the easiest of jobs to head the ball past Fabianski.
The scoreline didn’t sway after that, though there was still time for Kroos to smash a shot into the post during extra time.
It was just reward for a clinical Bayern side who will now head into the second leg as strong favourite to progress.
For Arsenal it is yet another crushing blow after an opening period that had promised so much and they are finding their campaign slowly crashing around them.
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