The 10 Biggest Shocks in the History of the Champions League Last 16
With this season's Champions League round of 16 currently going through its paces, a bounty of clubs are looking to overcome the odds in the hopes of claiming a quarter-final berth.
It's not a feat that's gone unaccomplished in the past, and here we've compiled some of the biggest surprise results to have come out of this particular stage of the contest, be it from a single-leg spectrum or taking aggregate results into account.
Although the round of 16 is a Champions League format that's only been in effect since the 2003-04 season, our collection runs further back, incorporating some of those fixtures that emerged when the second group phase was still in place.
Impact of said result, difference in club stature and the strength of line-ups have all been taken into account in order to rank the biggest round of 16 shocks, but each and every entrant holds special significance in its own right.
10. Barcelona 4-0 Milan: 2012-13
1 of 10Date: March 12, 2013
Before the Barcelona side of 2012-13, no team had successfully reversed a 2-0 Champions League first-leg deficit without the help of an away goal.
Strictly speaking, given the vast strength of La Blaugrana's squad last term, there are some who may not dub this result a "shock," per se, but Milan's team were no pushovers, as was shown at the San Siro just three weeks prior.
Inside 40 minutes of the Camp Nou leg, the Kevin-Prince Boateng and Sulley Muntari finishes that had given the Rossoneri such hope from the reverse matchup were erased.
David Villa and Jordi Alba would eventually build on that Lionel Messi brace from the first half, turning what could have been a frightful night into one of supreme comfort.
9. Chelsea 4-1 Napoli (AET): 2011-12
2 of 10Date: March 14, 2012
It's frequently debated as to whether it's more preferable to play the away leg of any European fixture first or second, but Chelsea found that a return homecoming played into their hands during their 2011-12 campaign.
As the old adage goes, anything worth having is worth fighting for, and the Blues certainly did just that on their way to claiming that season's Champions League.
Andre Villas-Boas came under heavy fire for the 3-1 loss to Napoli in Naples, and by the time the Stamford Bridge leg came about, Roberto Di Matteo was the man in charge.
After 90 minutes, the English giants had managed to match that score, and a Branislav Ivanovic winner in the 105th minute would put the finishing touches on a most glorious comeback for Chelsea.
8. Deportivo La Coruna 4-3 Paris Saint-Germain: 2000-01
3 of 10Date: March 7, 2001
The Deportivo La Coruna side at the turn of the century was arguably the strongest in the club's history, the early 1990s also providing stiff competition for that honour.
However, during the penultimate season in which the second group stage was still a Champions League format, Javier Iruretagoyena Amiano's 2000-01 team showed precisely why they were a monolith not to be trifled with.
Paris Saint-Germain got some early revenge on the scoreboard for their 3-1 loss at home to Depor four months earlier, establishing a 3-0 lead at the Estadio Riazor through goals from Jay-Jay Okocha and a Laurent Leroy brace.
The second period saw the Spanish hosts kick things up a notch, however, and a Walter Pandiani hat-trick laid the foundations for a marvellous revival, Diego Tristan adding a fourth, crucial finish.
As a result, Depor would edge Galatasaray on goal difference at the top of their last 16 group before eventually bowing out to Leeds United in the quarter-finals.
7. Barcelona 1-2 Liverpool: 2006-07
4 of 10
Date: February 21, 2007
Liverpool are a club with a storied past in European football, and the early 2000s brought the Merseysiders their first string of real success on the continental stage since the illustrious dominance of the 1970s.
The 2006-07 season may have finished with the Reds settling for the runners-up spot behind Milan, but not before Rafa Benitez's side left their mark on a prestigious Barcelona team along the way.
Beginning their round of 16 encounter with La Blaugrana at the Camp Nou, Craig Bellamy and John Arne Riise reduced a Xavi opener to rubble, paving the way for a shock Liverpool victory in Catalan country.
Barca would go on to win 1-0 at Anfield in the return fixture, but two extremely precious away goals meant that it was the English club that progressed.
6.. Milan 0-1 Tottenham: 2010-11
5 of 10
Date: February 15, 2011
To this date, Tottenham have only competed in one season of Champions League football, but what a lasting impression they made during the 2010-11 term, upsetting not just one but both of the Milan titans.
Inter already tasted what the North Londoners—or more specifically Gareth Bale—were capable of during the group phase, but Milan got their round of 16 hopes off to a dismal start, losing 1-0 at home in the first leg.
Long gone are the days when one might see Peter Crouch bagging goals under the European spotlight, but an 80th-minute winner at the San Siro will certainly go down as one of the striker's career highlights.
This was an extremely talented Rossoneri outfit, too, and one that would go on to win that season's Serie A, but the likes of Zlatan Ibrahimovic, Thiago Silva and co. were left wanting against their debutant opponents.
5. APOEL Nicosia 1-0 Lyon (4-3 Penalties): 2011-12
6 of 10Date: March 7, 2012
Far from the glitziest of fixtures but a historic achievement for the Cypriot minnows all the same, APOEL Nicosia booked a place in the Champions League finals for the first time in their existence during the 2011-12 contest.
Alexandre Lacazette ensured that French staple Lyon took a 1-0 aggregate lead to the GSP Stadium, but Gustavo Manduca quickly decimated that deficit, netting just nine minutes into the return fixture.
From there, one might have favoured Lyon, the far more experienced of the pair and just coming off the back of an era of Ligue 1 dominance, to keep their cool and advance, but it was actually APOEL exerting a great deal of their own pressure.
Eventually the duo would have to endure extra time and a penalty shootout, where spot-kicks from Ailton Jose Almeida, Nuno Morais, Nektarious Alexandrou and finally Ivan Trickovscki were enough to seal a 4-3 penalty upset.
4. Real Madrid 0-1 Arsenal: 2005-06
7 of 10Date: February 21, 2006
Arsenal had all kinds of issues heading to the Bernabeu in 2006; Patrick Vieira's departure the year before had left a considerable void in the squad's engine room, and Thierry Henry's time as a Gunners was coming to its end.
Then, there were more immediate concerns for Arsene Wenger when it came to injuries, and the Frenchman was forced to face a line-up containing Ronaldo, Zinedine Zidane, Robinho, David Beckham and other superstars with a crocked defensive party.
Tactics would win out for Wenger, though, and Henry managed to nick a goal while the make-shift back line held up their end of the bargain, somehow scraping a 1-0 win from the Spanish capital.
Incredibly, Arsenal would once again restrain Real's offensive powerhouses in the return leg, their 1-0 aggregate triumph seeing the La Liga giants out of the competition.
3. Spartak Moscow 4-1 Arsenal: 2000-01
8 of 10Date: November 22, 2000
Spartak Moscow came into the 2000-01 second group stage as a fearsome outfit, maintaining a 100 percent winning record in the group stage and materialising a fortress in their own backyard.
However, the visit of Arsenal was nevertheless a daunting task for the Russians, Wenger's men having found themselves in some domineering form that campaign, too.
That being said, scores from Igor Titov, Luis Robson and a double courtesy of Marcao meant that the dreams of reliving any European glory years were kept alive.
That would be the only win Spartak managed in the second group stage that season, losses to the Gunners, Lyon and Bayern Munich on two occasions showing that the success was indeed short-lived.
2. Monaco 0-2 PSV Eindhoven: 2004-05
9 of 10Date: March 9, 2005
Long before the big-money investments of present were ever a thought on the French Riviera, Monaco welcomed PSV Eindhoven to France in the 2004-05 Champions League, having made the final of the previous year's competition.
Monaco topped a tough group containing Liverpool, Olympiakos and Deportivo La Coruna in the group phase, while their Dutch opponents had to settle for second-best behind Arsenal in their pool, Panathinaikos and Rosenborg losing out.
However, all on-paper form appeared to count for nought as Monaco failed to overcome the 1-0 deficit established in the first leg in Holland, losing out by an even bigger margin on home soil.
Jan Vennegoor of Hesselink and DaMarcus Beasley took on the roles of heroes at the Stade Louis II, and although their European trail would eventually end in the semi-finals, the Eredivisie championship would provide the club with some comfort that term.
1. Real Madrid 0-5 Liverpool (Agg.): 2008-09
10 of 10Date: February 25 and March 10, 2009
For the fifth time in five seasons, the round of 16 was the marker at which the Champions League campaign ended for Real Madrid, their 2008-09 hopes crumbling at the hands of a resurgent Liverpool side.
It's difficult to argue which of the two-legged affair's results was the more surprising—Real's 1-0 loss at home to the Reds or a highly unsuccessful 4-0 demolition at Anfield.
This was a Liverpool team that finished second in the Premier League that season and were enjoying a run of challenging for titles both domestically and in Europe, but the fashion in which this fixture was decided left mouths agape nonetheless.
Yossi Benayoun was the man who prodded Liverpool into an all-important lead in Madrid, but additions from Fernando Torres, Andrea Dossena and Steven Gerrard on two occasions in the home leg capped off a remarkable statement.
