Is this Arsenal boss Arsene Wenger's last shot at Champions League glory?
Arsene Wenger will take charge of his 177th Champions League match when Arsenal face Bayern Munich in the Allianz Arena on Wednesday, painfully aware that the 178th may well turn out to be his last.
The Arsenal manager might yet stay on at the Emirates beyond the end of this season, taking his reign past the 21-year mark, but the old certainty of the North London giants securing Champions League football -- regardless of their performance in the competition itself -- is no longer quite so secure as it has been over the past decade-and-a-half.
With the 2016-17 Premier League campaign giving us the most intense battle yet for Champions League qualification, Arsenal's participation in next season's competition is by no means guaranteed, so there really is no time like the present for Wenger and his players to seize the day when they face the German champions in Bavaria.
After almost 20 attempts at landing the big one, Wenger might just be preparing for his final assault on the European Cup when he sends out his players for Wednesday's round-of-16 first leg.
But has the moment passed? Is Wenger destined to enter the history books as the greatest coach never to win the Champions League?
All of his contemporaries have at least one to their name.
Bayern coach Carlo Ancelotti has three continental triumphs on his résumé. Sir Alex Ferguson, Ottmar Hitzfeld, Vicente del Bosque, Jose Mourinho and Pep Guardiola have two apiece, while Rafa Benitez, Louis van Gaal, Luis Enrique, Zinedine Zidane, Marcelo Lippi and even Roberto Di Matteo are all able to reflect on their careers having guided their respective teams to one Champions League title.
Wenger is the glaring omission.
A football visionary who transformed not only his club, but also acted as the catalyst for an entire cultural change in the English game, can only point to one appearance in a Champions League final throughout his time at Arsenal.
One final, which ended in defeat to Barcelona in Paris in 2006, and a whole lot of disappointment.
But it is too easy to sneer at Wenger's European record and dismiss him as a coach who has fallen short too often when pitted against the elite managers of his generation.
In recent years, he has quite simply failed to keep pace with the changing face of the game from a tactical perspective, with his Arsenal team possessing all the aesthetic beauty of Barcelona, but entirely lacking their steel.
They have been outmuscled and outplayed by Bayern, twice being eliminated by the Germans in the first knockout round in recent years, and even when the draw has been favourable, as against AS Monaco in 2014-15, Arsenal still managed to make a mess of things.
But during his first decade in charge, Wenger created a formidable team which simply failed to deliver when the moment was there for them to become Europe's best.
Back in 2003-04, Wenger's "Invincibles" perhaps saw the club's best chance evaporate when eliminated by Chelsea in the quarterfinals in a year when Benitez somehow carried a vastly inferior Liverpool team to Champions League glory.
Twelve months on, reduced to 10 men for much of the final against Barcelona, Arsenal lost 2-1 in the Stade de France with a team that would have been worthy European champions.
Since that night in Paris, it has been a perennial tale of woe for Wenger and Arsenal.
Overpowered by Manchester United in the 2008-09 semifinal, Arsenal's track record since has been woeful, with Wenger unable to guide the club past the round of 16 since the 2009-10 campaign.
True, Arsenal have too often come up against Barca and Bayern at this stage, but failure has almost become accepted on the basis that they have simply been unlucky in the draw.
So are there any positives for Wenger and Arsenal to cling onto as they embark on potentially the manager's final Champions League campaign?
The last time Arsenal emerged unbeaten from their group, as they did this season, was in 2005-06 when they progressed to the final.
And for all of their recent shortcomings in the Premier League, Arsenal will face a Bayern team that has replaced flair with functionality under Ancelotti, so the formidable Bayern of the Guardiola era is now a less fearsome animal.
Bayern do go into the game on the back of 15 successive Champions League home wins -- a tournament record -- but Arsenal have recent memories of winning at the Allianz following the 2-0 victory in March 2013 (just don't mention the 5-1 defeat in November 2015).
Wenger, 67, may yet surprise us all by continuing at the helm for years to come, emulating Ferguson by managing beyond his 70th birthday. But if Arsenal miss out on qualification next season, it will be a long wait until he gets another crack at the Champions League.
Raymond Goethals guided Marseille to Champions League success aged 71 back in 1993, so Wenger can at least comfort himself by the fact that men older than him have won the competition.
But once a club is out of the Champions League, it is so much more difficult to get back into it, as previous winners such as Liverpool, United, AC Milan, Inter and Marseille have discovered in recent years.
Arsenal and Wenger are clinging to the Champions League rock-face, but their grip is beginning to loosen.
So it might just be a case of now or never for Wenger this season. He may not get another chance.
Mark Ogden is a senior football writer for ESPN FC. Follow him @MarkOgden_