The promised land of the Champions League knockout rounds awaits Arsenal yet again, as the North London behemoths pit their wits against Porto in Wednesday's last-16 first leg at the Estadio do Dragao.

Following a few years in the unfancied Europa League - where continental success continued to elude them - the Gunners are earning their stars at the top continental table again and made it through Group B as section winners with a game to spare.

A historic Premier League and Champions League double also remains a distinct possibility for Mikel Arteta's free-scoring charges too, but in order to break new ground in Europe, they must first break a curse that has haunted them for over a decade.

Arsenal's most recent last-16 triumph in the Champions League actually came against Porto, although that was all the way back in the 2009-10 campaign, and the beaten 2006 finalists have since had their dreams crushed at this point seven times on the trot.

As the current youthful crop endeavour to banish their last-16 demons, Sports Mole takes a deeper dive into Arsenal's previous failures to make it to the Champions League quarter-finals.

2010-11 - Barcelona 4-3 Arsenal

After putting five past Porto without reply at the Emirates to punch their ticket to the 2009-10 quarter-finals, Arsenal succumbed to Barcelona's supremacy at Camp Nou after a hard-earned 2-2 Emirates draw, where Cesc Fabregas memorably struck from the spot with a broken leg.

Fast-forward another year, and despite the best efforts of his Spain teammates - who forced him into a Barcelona jersey during their 2010 World Cup celebrations - Fabregas continued to pull the strings in the Arsenal midfield, who would outclass Pep Guardiola's maestros at the Emirates in the 2010-11 last 16.

Even though David Villa beat the offside trap to draw first blood in North London, Arsene Wenger's men got back on terms through an incredible Robin van Persie strike from a tight angle, before diminutive Russian Andrey Arshavin left Victor Valdes on his backside with one of the most iconic goals to fly into an Emirates net.

Arshavin's winner, Guardiola's dejection and Jack Wilshere's spellbinding performance were all highlights of the evening for the men in red, who were less than an hour away from reaching the quarters at Camp Nou, where a Sergio Busquets own goal cancelled out Lionel Messi's opener.

However, injustice would soon prevail, as referee Massimo Busacca brandished a second yellow to Van Persie for kicking the ball away; a bookable offence under the current rules, but a farcical decision back then, especially with Van Persie affirming that he had not heard the official's whistle go.

Wenger's 10 men fought valiantly, but Xavi would restore Barca's lead before Messi's second of the night arrived from the penalty spot, marking the start of a prolonged sequence of last-16 heartbreaks for their incandescent foes.

2011-12 - AC Milan 4-3 Arsenal

Fabregas would indeed be donning the Barcelona jersey by the time the 2011-12 season commenced, but with Van Persie now establishing a reputation as one of the Premier League's fiercest marksmen, Arsenal had reason for optimism against AC Milan.

The Rossoneri were hardly as intimidating as the glory teams of old, but Massimiliano Allegri's unit were too hot for Arsenal to handle in their last-16 first leg at San Siro, where the disgraced Robinho netted twice alongside Zlatan Ibrahimovic and Kevin Prince-Boateng.

Milan had already fallen victim to the famed miracle of Istanbul, though, and the Rossoneri were on the cusp of being taken to extra time in the miracle of North London, where Laurent Koscielny, Tomas Rosicky and Van Persie sent Arsenal three goals ahead by half time.

However, Allegri's defence shut up shop in the second period to ensure that Arsenal's powers of recovery would prove insufficient; while Wenger's men won the battle, Milan won the war.

2012-13 - Bayern Munich 3-3 Arsenal (Bayern win on away goals)

With Van Persie swapping the red of Arsenal for the red of Manchester United at the end of the 2011-12 season, Arsenal began their latest Champions League venture in the distinct absence of a big-name superstar, but with the likes of Santi Cazorla, Theo Walcott and Lukas Podolski stepping up in the Dutchman's absence.

Former Bayern Munich man Podolski would make the net bulge against his former team at the Emirates in their last-16 first leg, but only after Thomas Muller and Toni Kroos had breached Wojciech Szczesny's net, and Mario Mandzukic put the cherry on top in the dying embers.

The writing was ostensibly on the wall as Arsenal made the daunting trek to the Allianz Arena for the return fixture, but the Bayern faithful were sitting a little uneasy just three minutes in, when Giroud began the Gunners' renaissance.

A scoreless 82 minutes followed before Koscielny got Arsenal back on level terms regarding the aggregate scoreline, but owing to the now-abolished away goals rule, another praiseworthy European fightback from Wenger's charges was in vain.

2013-14 - Bayern 3-1 Arsenal

After subjecting Arsenal to more last-16 heartache, Bayern would enjoy another successful London sojourn at the conclusion of the 2012-13 Champions League, sinking Bundesliga foes Borussia Dortmund to confirm their status as Europe's top dogs.

Once again, the Gunners' reward for progressing through the group stage would be a last-16 tie against the defending champions, who conceded a penalty in the opening 10 minutes of their first leg at the Emirates, but Mesut Ozil's tame effort was meat and drink for Manuel Neuer.

David Alaba also fluffed his lines from 12 yards before the half-time whistle blew, but his blushes were soon spared by Kroos and Muller, the latter of whom capped off a two-goal Emirates success with a clinical diving header in front of the travelling Bavarian contingent.

As was apparently customary with Wenger-led teams back then, Arsenal performed far better in the second encounter - where Podolski cancelled out a Bastian Schweinsteiger opener and Lukasz Fabianski stopped Muller's injury-time penalty - but shortcomings in the first leg proved costly for the third year running.

2014-15 - Monaco 3-3 Arsenal (Monaco win on away goals)

Growing sick of the sight of Bayern jerseys, Arsenal would welcome a break from Bavarian battles for the last 16 of the 2014-15 Champions League, where Wenger would test his mettle against one of his erstwhile employers in Monaco.

The reigning FA Cup champions would have the luxury of playing the first leg at home for the third year running, but the Emirates crowd were left agitated by the full-time whistle once again, as ex-Tottenham Hotspur man Dimitar Berbatov, Geoffrey Kondogbia and Yannick Carrasco struck on London soil.

Alex Oxlade-Chamberlain's injury-time effort would at least give Arsenal something to build on before the subsequent trip to the Stade Louis II, in which a quintessential last-16 fightback saw Giroud and Aaron Ramsey breached the Monegasques' net without reply.

The all-important third that Arsenal so craved did not arrive, though, forcing the Gunners to pack their bags and wave goodbye to the Champions League for yet another year owing to Monaco's away goals, and this one left a particularly bitter taste in the mouth.

2015-16 - Barcelona 5-1 Arsenal

Renewing hostilities with Barcelona for the first time since their controversial 2010-11 last-16 exit, Arsenal intended to serve a cold dish of revenge at the Emirates in the first leg of their 2015-16 battle, but lightning would not strike twice for the Blaugrana in the English capital.

Luis Enrique's men endured 70 minutes of frustration before the irrepressible Messi haunted the Gunners once more, finishing off a slick move involving the two other members of the celebrated trinity, Luis Suarez and Neymar, before being scythed down by Mathieu Flamini inside the box.

The eight-time Ballon d'Or winner calmly sent Petr Cech the wrong way to double the holders' advantage, and the tie was seemingly a foregone conclusion just 18 minutes into the second leg, where Neymar got the Camp Nou crowd off their seats.

A stunner from Mohamed Elneny - the only surviving member of Arsenal's last CL knockout squad - gave Wenger's team a miniscule flicker of hope, which Suarez and Messi immediately extinguished, as Arsenal lost both legs of a Champions League last-16 tie for the first time ever.

2016-17 - Bayern Munich 10-2 Arsenal

With their laudable streak of Premier League top-four finishes at risk of coming to an end in the 2016-17 season, lifting the Champions League trophy aloft would have been Arsenal's best route back into the premier tournament for 2017-18, but they would have to right several wrongs against Bayern to even progress to the last eight.

The Gunners had not been embarrassed at the Allianz Arena in 2012-13 or 2013-14 by any stretch, and the first 45 minutes of their opening encounter in 2016-17 would have left Wenger the happier manager, as Alexis Sanchez responded to an Arjen Robben opener.

However, after Koscielny was withdrawn injured early in the second half, a demolition job commenced, as Thiago Alcantara's brace, Robert Lewandowski's header and Muller's strike condemned the Gunners to a 5-1 shellacking on Bavarian soil.

Wenger's men once again showed a sliver of life in the second leg when Walcott opened the scoring, but in eerily identical fashion to the first leg, the loss of Koscielny - this time due to a red card - was the catalyst for a second-half Bayern battering.

Lewandowski and Robben both made their mark again, as did Arturo Vidal (two) and Douglas Costa in another 5-1 pummelling - still Arsenal's heaviest loss at the Emirates Stadium to date, and one which would prove to be Wenger's final Champions League match on the North London touchline.