There are two options for how Wenger's 22-year reign will end, one of them being at tea time at the John Smith's Stadium on May 13th and the other at the Parc Olympique Lyonnais in Lyon, the latter of which would bring the beleagured boss one last chance at European glory.
Arsenal's European record under Wenger is one of the club's greatest disappointments, with just once final and one semi-final appearance during his tenure.
Indeed, in the last eight seasons, Arsenal have failed to get beyond the Last-16.
It is very much last chance saloon for Wenger and whilst the Europa League is very much seen as a second-tier trophy these days, it remains a European title, something Wenger has never won at Arsenal, having previously tasted defeat in the UEFA Cup final in 2000, losing to Galatasaray.
Thursday will be Wenger's 250th European game and it could prove key in how his side's European adventures are remembered.
Wenger's domestic achievements will never be forgotten, with his record of FA Cup titles likely to take some beating and the Invincibles alone likely to remain in the wider public consciousness forever.
However, Arsenal have always been a different animal in Europe, a tame housecat, even when they were were a proud lion that stood atop English football as undisputed king.
Should they fail in Madrid, it is the crushing defeats to Bayern Munich, the disappointment of 2006 in Paris when it looked for all the world like the European drought would be ended and that loss in Copenhagen in 2000 that the fans will remember and not the stunning victories over Inter Milan and Real Madrid when both sides were in their prime.
The odds are stacked against Arsenal though, having failed to claim a point on the road in 2018 is there any hope that they can go away to one of the most disciplined sides in Europe and spring a surprise?