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Over the course of the next eight days, Europe’s top 16 teams will be whittled down to only eight as the quarter-finalists of the Champions League are decided.
The Champions League’s expansion in 2003-04 doubled the number of teams in the competition and thereby doubled the number of teams who reached the knockout phase. As a result, that was the first time since the reinvention of the competition that there was a classic round of 16.
Just as the big guns typically find their way through the group stage unharmed, they also tend to come through the first elimination round without too many issues, though over the years there have been instances of giant-killing.
Manchester City, Liverpool and Bayern Munich already have one foot in the final eight, given the emphatic nature of their first-leg victories, but five places are up for grabs.
Shocks at this stage of the season are not commonplace and the potential for any genuine upsets this year is slim. Shakhtar Donetsk have a strong chance of upsetting Roma, while Sevilla and Chelsea are very much in their ties against Manchester United and Barcelona respectively.
Here are five of the greatest upsets at this juncture of the competition.
#5 FC Porto v Manchester United (2003-04)
Jose Mourinho’s Porto might have been UEFA Cup holders when they were pitted against Manchester United but they were not given much of a chance against far more seasoned European opponents, who contained the likes of Ryan Giggs, Paul Scholes and Roy Keane.
Certainly, in the early minutes of the first leg, it looked like a routine success for United. Scholes might have seen his free kick stopped, but Quinton Fortune fired home the rebound. Sir Alex Ferguson’s side had not conceded in five European matches but Benni McCarthy scored twice to turn the tie on its head.
In the return leg, United took a stranglehold of the tie in the opening half as they got the better of a war of attrition that would become a Mourinho trademark in the years to come. Paul Scholes put the home side ahead of away goals and on the stroke of half-time had a goal fatefully and wrongly disallowed for offside.
United chased a second goal, throwing on Cristiano Ronaldo for defensive midfielder Darren Fletcher, but in the last minute, Tim Howard fumbled a routine free kick, which allowed Francisco Costinha to pounce.
Mourinho, whose side went on to win the competition by beating Monaco in the final, famously celebrated by sprinting down the touchline, and his rivalry with Ferguson had begun.
#4 Lyon v Real Madrid (2009-10)
Real Madrid have not always been the all-conquering force in Europe, despite their record 11 titles. For a spell in the early part of the millennium, they suffered a remarkable jinx as they were unable to get past the quarter-final phase.
Manuel Pellegrini’s side had impressed in the group phase, steamrollering their way to the top of the standings with a succession of strong victories, seeing off Milan, Marseille and Zurich in the process. In La Liga, meanwhile, they were looking good, even in comparison to a formidable Barcelona team, and even a shock upset against Alcorcon in the Copa del Rey did not suggest they would find an ailing Lyon side too much of a hurdle.
At Stade Gerland, however, a goal from Jean II Makoun shortly after the interval gave the French side an advantage to carry to Spain three weeks later.
The world seemed to have been put to rights when Cristiano Ronaldo struck after six minutes for the hosts, yet 15 minutes from time Miralem Pjanic, a product of the OL youth system, carried the French side to perhaps their most famous ever success.
It was to prove a season of frustration for Los Blancos, who won 18 of their last 20 matches in La Liga but still finished second to Barca, despite picking up 96 points.
Lyon, meanwhile, saw off Bordeaux in the quarter-finals but came unstuck against Bayern Munich in the quarter-finals.
#3 Tottenham v AC Milan (2010-11)
If Spurs were to face Milan today, there would be no contest that the Premier League side would start as a hot favourite. Rewind seven years, though, and the story was very different.
Tottenham, under the guidance of Harry Redknapp, were just building to become the force they are today. Gareth Bale was starting to emerge as a superstar, aided by a stunning performance against Inter in the group stages, in which Spurs had bettered the defending champions.
There were still questions about their temperament and experience when they went to San Siro for the first leg of their last-16 encounter. Spurs had not played in the European Cup since 1962, when their manager was just 15, and had precious little experience, while in the group stage they had failed to achieve a single away win.
They confounded their critics, then, by winning in Italy, with Aaron Lennon setting up Peter Crouch to score with 10 minutes remaining. More memorable, though, was Redknapp’s assistant Joe Jordan squaring up to Milan hardman Gennaro Gattuso after the game.
Zlatan Ibrahimovic, Pato, Robinho & co. were unable to square the game back at White Hart Lane, despite a siege on the home goal in the first half that saw William Gallas made a crucial clearance off the line.
The adventure that season would not last much longer – Real Madrid easily accounted for them in the quarter-finals – but in many ways, it was just beginning for the club.
#2 APOEL v Lyon (2011-12)
This may not be the highest profile upset on this list, yet APOEL’s victory over Lyon could be considered one of the most stunning. Cypriot football has never enjoyed a prominent position among the European elite, yet they took a place in the final eight of the Champions League when the minnows stunned opponents who had reached the semi-finals less than 12 months earlier.
Really, there should have been few issues for the Ligue 1 side, particularly after they claimed the first leg 1-0 thanks to a strike from Alexandre Lacazette just before the hour mark.
The advantage looked to be a good one, particularly as OL had not conceded an away goal that could have had the potential to make their life tricky.
Back in Cyprus, however, Gustavo Manduca scored early for the hosts. Although the French side outplayed them thereafter, they could have few complaints about going to extra-time in what had been a surprisingly evenly balanced tie.
Manduca was dismissed during that period, yet APOEL survived to force penalties. The first six takers all converted but Lacazette missed. After Ivan Trickowski scored for the hosts, Michel Bastos had to do likewise to keep Lyon in the tie but fluffed his lines.
In the quarter-finals, Real Madrid made light work of their opponents but were made to work for their win in Nicosia. After Karim Benzema scored 15 minutes from the end, it was largely one-way traffic, with the Spaniards running out 8-2 victors on aggregate.
#1 Monaco v Arsenal (2014-15)
Just as Arsenal were expected to take a big step into the quarter-final phase of the Champions League, having been handed what many expected to be the easiest tie of the last 16, they suffered a crushing and embarrassing defeat.
The warning sides should have been heeded, however. While Monaco had won their group ahead of Bayer Leverkusen, Zenit St Petersburg and Benfica, Arsenal had finished second to Borussia Dortmund. Still, they went into the tie buoyant, having avoided any of the big guns.
That feeling of optimism soon vanished. At the Emirates Stadium, Monaco executed a perfect counterattacking game. Geoffrey Kondogbia gave them the edge before the break and early in the second half, Dimitar Berbatov put Monaco firmly in control.
When Alex Oxlade-Chamberlain struck in stoppage time at the end of the match, it seemed that the crisis had been averted, yet the Gunners self-destructed as they somehow allowed Yannick Ferreira Carrasco, superb on the night, to cap a famous victory for Leonardo Jardim’s side.
Arsenal played much better in the second leg, with goals from Olivier Giroud and Aaron Ramsey giving them a 2-0 win on the night, but yet were still eliminated on the away goals rule.
While such losses have become commonplace for Arsenal fans in recent years, going out to Monaco came as a stunning shock. it may not have been the beginning of the end for Arsene Wenger at Arsenal, but it certainly accelerated the Gunners’ decline.
