Ten-man Arsenal were knocked out of the Champions League at the last-16 stage for the seventh successive season following a second-half 5-1 humiliation by Bayern Munich at the Emirates Stadium.
A controversial decision in the 53rd minute by the referee shattered any hopes of the Gunners becoming the first side in Champions League history to overturn a four-goal deficit.
They led through Theo Walcott’s stunning 20th-minute goal, before Bayern were awarded a penalty that also resulted in the sending off of defender Laurent Koscielny.
The France centre-back was initially shown a yellow card by referee Anastasios Sidiropoulos for his foul on Robert Lewandowski inside the area – but it was upgraded to a red once he realised Koscielny made no attempt to win the ball.
Gunners boss Arsene Wenger looked perplexed by the sudden change of heart by the official. And the call was a turning point in the match.
Lewandowski placed his spot-kick beyond the reach of David Ospina to give Bayern a 6-2 aggregate lead and effectively kill off the tie.
The home side then folded as Bayern scored three goals in 12 minutes. Arjen Robben robbed Alexis Sanchez of the ball before Douglas Costa made it 3-1 with a stunning solo goal.
Fellow midfielder Arturo Vidal grabbed a late double, first with an impudent chip before slotting in from Costa’s square pass.
If this was to be Wenger’s final outing in the Champions League with Arsenal then what an embarrassing final act.
Few expected the Gunners to perform a miracle, but they did at least expect to take the fight to the German giants.
Aside from the goal, Walcott also went close when Manuel Neuer saved his effort and Olivier Giroud hit the base of the post with a header.
Walcott was also denied a penalty after it appeared that Xabi Alonso had fouled him.
But Bayern rarely looked stretched and bid their time before punishing an error-strewn second-half display by the home side.
In another match also played on Tuesday, Madrid came from a goal down against Napoli in the second leg of their Champions League last-16 tie to progress to the quarter-finals, for the seventh successive season.
Napoli were utterly dominant in a one-sided first half and took the lead on 24 minutes when Marek Hamsik put Dries Mertens’ through on goal as Real’s defence went missing.
But captain Sergio Ramos netted two headers in six minutes after the break to put the defending champions in control.