Arsene Wenger will face his easiest Champions League knockout tie since 2010 when his former club AS Monaco roll into town.
Despite finishing second in their group behind Borussia Dortmund, the Gunners finally avoided the big guns of Europe to draw a club with an average attendance of 7,000 people.
Since thrashing Porto 6-2 on aggregate in the round of 16 in 2010, Arsenal have been knocked out by Barcelona, Bayern Munich (twice) and a Zlatan Ibrahimovic-inspired AC Milan in the same round. It has been an excruciating spell of complete inadequacy from the perennial qualifiers and unachievers of Europe's premier competition.
"We have had 17 consecutive seasons in this competition. 'Easy' is a word you need to ban in the Champions League," Wenger told reporters today.
The 17th consecutive season in the Champions League - what a record. It's one that cannot be bettered by any other club in Europe. But those 17 seasons have reaped just one appearance in the final and just another in the semi-finals.
Wenger has regularly spoken of the importance of qualifying for this competition where TV revenue takes its invitees head and shoulders above the less privileged, but concern for whether Arsenal can win it has been curiously absent.
Specialist in failure
It is almost as if Wenger cashes in his chips as soon as the group stages are reached, only to refocus on achieving the same feat once again for next season. But the record speaks for itself. He is the specialist in failure, at least when it comes to Champions League football.
Those famous words, spoken by Jose Mourinho at this time last year, were met with uproar from the Emirates. In many senses, Wenger has been anything but a failure at Arsenal. He has taken them from a decent club to one of the world's biggest. The Emirates Stadium and Arsenal's huge revenue is as much a part of his legacy as his three Premier League titles, his Invincibles record and his five FA Cup winner's medals.
But the lack of a Champions League trophy, despite so many attempts, is bound to speak louder when his time in the north London hot seat comes to an end.
A spectacular record
Wenger will take charge of his 110th Champions League game on Wednesday evening since the round of 16 was introduced in 2003. For a man still waiting for his first title, that is a staggering amount of games.
The next most experience manager to not win the trophy is Roberto Mancini with 61 games. With the Italian currently managing Inter Milan, he is only streaming further into the lead. It is a similar story on the club side of things with Arsenal playing the most seasons of Champions League football since it was reformatted without winning it. Olympiakos (14) are the next most prominent underachievers.
Arsenal folklore describes the 2003/04 season as being their best chance to win it. The Invincibles squad was arguably the best in Europe and all of the big boys had been knocked out. They fell to Chelsea in the quarter-final with Jose Mourinho's Porto beating Monaco in that year's final.
Their 2006 run to the final was just the law of averages playing out. Spin the wheel enough times and eventually the ball will land on the number you want. They came close, leading Barcelona by a single goal all the way 76th minute, but ultimately failed once again.
Light at the end of the tunnel
From then on Arsenal only grew weaker. Just qualifying for the tournament became a monumental struggle and, one day, Wenger will be applauded for keeping them in it under such intense austerity. But now there are few excuses. They have money to spend on the likes of Mesut Ozil and Alexis Sanchez and a squad brimming with talent.
Sanchez can unlock the best defences in the world on his own. Ozil can provide the pass if he can't. Even Olivier Giroud is becoming the powerhouse centre-forward no one expected him to be. Santi Cazorla, Aaron Ramsey and Theo Walcott can all impress on their day as well.
This may not be the squad to beat Real Madrid and Bayern Munich, but it certainly has the quality to brush aside a team like Monaco.
Arsenal's win record of 35.1 per cent in the knockout stages of the Champions League is dyer and must be improved before Wenger leaves. Saying this game is not easy is diplomatic, but deep down the Arsenal boss knows anything but progression into the quarter-finals will be another gross underachievement.
If they can make the semi-finals this year it may build confidence in this competition; confidence that was once present but has been knocked out of them over the last four years.
A Champions League triumph, though seemingly impossible this season, is at least feasible in the next three years. Arsenal will only grow stronger with each transfer market and a manager of Wenger's reputation has little excuse for not building another title-winning squad.
Wenger's legacy in football, not just at Arsenal, is dependant on success in this competition.