A shell-shocked Real Madrid have recorded a surprise unwanted feat for the first time in 16 years, following their 3-0 defeat at Arsenal this evening.
Declan Rice's two extraordinary free kicks set Mikel Arteta's men on their way, before Mikel Merino added a third shortly after to put the tie almost out of reach even at the halfway point for Los Blancos.
A cagey first half saw the sides go in at the break goalless, but Rice's delightful double set the Emirates Stadium alight, with Merino's strike adding some gloss, and breathing space, ahead of the second leg at the Santiago Bernabeu next week.
The inquest will already have begun in the Spanish media, with Carlo Ancelotti's future in the role now in serious doubt, especially after the weekend's defeat at home to Valencia.
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Real set near-two-decade low in Emirates humbling
After also failing to find the net across 120 minutes in the second leg of their last-16 tie with Atletico Madrid, that means Real Madrid have gone two successive Champions League games without scoring for the first time since 2009.
On that occasion, Juande Ramos's Real were knocked out in the last 16 by Liverpool, losing 5-0 on aggregate.
Real were beaten 4-0 at Anfield in the second leg of that tie, and tonight's defeat was as humbling as any result they have suffered in the competition since, with Arteta's men deserving of their three-goal win.
It is also the first time since that tie with Liverpool in 2009 that Real Madrid have allowed 11 shots on target against them in a Champions League match, with all seven of Arsenal's efforts in the second half either finding the net, requiring an intervention from Thibaut Courtois, or a clearance from the goalline.
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Will the same fate beset Ancelotti as Ramos?
Ramos had only spent two months in the job before their elimination to Liverpool, and from that point on, the writing was on the wall, as he then left at the end of the season.
It feels as though Ancelotti will be heading in the same direction, especially given the intense rumours that have been swirling around about his future this season.
Saturday's shock defeat at home to Valencia has also scuppered their chances of retaining the La Liga title, meaning their season could now hinge solely on the Copa del Rey final against Barcelona at the end of the month.
It would be foolish to write Real Madrid off in the Champions League, no matter the circumstances, but this now looks an impossible task, and the Copa del Rey is unlikely to be enough for Ancelotti to keep his job.
Andrew Delaney
