It was inevitable, wasn't it?
After Arsenal overcame losing three of its first four group games in the Champions League only to rally and get the necessary results (and help) in the final two, the Gunners advanced to the round of 16. With Bayern Munich in Arsenal's group, the London side couldn't possibly face the Germans for a third time in four seasons in that stage, but that didn't prevent Arsene Wenger's charges from drawing the other worst-case scenario.
In order for Arsenal to avoid falling for a sixth straight time in this knockout stage, it will have to overcome defending champion Barcelona. It will be a rematch of the 2006 Champions League final and a rematch of their round-of-16 clash in 2010-11, which kicked off the current stretch of five straight last-16 ousters. Barcelona won the first leg 2-0 in London, creating an even steeper hill for the Gunners.
The failures in the round have been torturous and mind-numbing to Arsenal's supporters, with the club often digging itself a massive hole only to come within the closest possible margin before ultimately falling short. Here's a look back at Arsenal's last five round-of-16 failures ahead of what may be their toughest challenge yet:
2010-2011: Barcelona (4-3 aggregate)
On the heels of being ousted by Barcelona (and Messi's four-goal masterclass) in the quarterfinals the year before, Arsenal held a 2-1 lead after the first leg, battling back with late goals from Robin van Persie and Andrei Arshavin and led 3-2 on aggregate as the second leg at Camp Nou wound down. Then, van Persie, sitting on a yellow card, took a shot well after the offside flag was raised and got controversially sent off, with referee Massimo Busacca not hesitating to send off the Dutchman in the 56th minute.
Barcelona made sure to kick the wounded 10-man Gunners while they were down. Xavi's 69th-minute goal was followed two minutes after by a Lionel Messi penalty, as Barcelona seized control en route to a 4-3 aggregate triumph on the road to lifting the trophy.
2011-2012: AC Milan (4-3 aggregate)
Arsenal was left for dead after a 4-0 first-leg loss in Milan, as Kevin-Prince Boateng, Robinho (twice) and Zlatan Ibrahimovic poured it on at the San Siro. The Gunners had no shot, right? But then something funny happened at the Emirates. Arsenal did just enough to keep its fans with fleeting hope, scoring three before halftime in the second leg to pull within 4-3. That's as close as it got, as Christian Abbiati denied Gerinvho and van Persie in succession to preserve the lead and send Arsenal out. Just brutal.
2012-2013: Bayern Munich (3-3 aggregate, Bayern wins on away goals)
Bayern won 3-1 in London to take a sizeable advantage going home for the second leg, and it turned out to be just enough. Arsenal won the second leg 2-0, an impressive accomplishment in its own right, except that conceding three at home proved to be the deathblow.
Arsenal fell on away goals, and Bayern was on its way to another Champions League title.
2013-2014: Bayern Munich (3-1 aggregate)
Arsenal again fell by two at home in the first leg, allowing Bayern to waltz out of London with a 2-0 win after second-half goals by Toni Kroos and Thomas Muller. Bastian Schweinsteiger's 55th-minute goal padded the lead in the second leg, and even though Lukas Podolski put Arsenal on the board a couple of minutes later, the Gunners would get no closer. Another year, another last-16 disappointment. At least this one wasn't as gut-wrenching.
2014-2015: Monaco (3-3 aggregate, Monaco wins on away goals)
Of all the letdowns in this round, this one had to be the most disappointing, if only because Arsenal was the favorite despite being a second-place finisher. Arsenal, at last, got a favorable draw (so we all thought), against a Monaco side that had loaned and sold off the two prime assets that got the club to the Champions League to begin with in Radamel Falcao and James Rodriguez.
That didn't prevent the club from–again–blowing it at home in the first leg, this time to one of Wenger's former clubs. A 3-1 loss was compounded by an injury-time concession right after Alex Oxlade-Chamberlain had scored, which encapsulated the roller-coaster of Arsenal emotions perfectly. As anyone following Arsenal recently could have predicted, the Gunners did just enough to restore hope among their fans before gutting them, winning 2-0 in the second leg at Monaco but falling on away goals.
Any guesses as to how this season's round of 16 will unfold for the club?