5 of the greatest Champions League Round of 16 upsets

Champions League is back!
Champions League is back!

The Champions League returns next week with the first set of the Round of 16 matches. The marquee matches might be Real Madrid vs Paris Saint Germain and Chelsea vs Barcelona, but there are quite a few ties where underdogs can announce their intentions.

Basel will hope to conjure some magic when they take on heavy favourites Manchester City, Besiktas will also start as outsiders - despite finishing the group stages undefeated - when they take on German giants Bayern Munich.

The first knock-out stage has traditionally been the moments when giant-killers make their presence felt and this article takes a look at the five greatest Champions League upsets in the Round of 16 over the years.


5. PSV Eindhoven 2 - 1 Arsenal: 2006-07

Alex would score the decisive goal in PSV's victory over Arsenal in 2006-07

Alex would score the decisive goal in PSV's victory over Arsenal in 2006-07

The mid-2000s saw English clubs dominating the UEFA Champions League. Fresh from the 2005-06 campaign where they went all the way to the final, Arsenal were considered to be one of the favourites for the title the ensuing year. That didn't go quite according to plan.

Three English teams would make the semifinals that year, but Arsenal would be dumped out in the first knockout stage by Dutch side PSV Eindhoven. Despite having a better European pedigree than Arsenal, PSV's victory was considered a major upset.

In the first leg, the Arsenal side comprising of Thierry Henry, William Gallas and Freddie Ljungberg dominated the proceedings at the Philips Stadion till half-time - but Ronald Koeman's PSV changed the tide after the break. Edison Mendez beat Jens Lehmann to give the hosts a 1-0 advantage to take to London.

Needing two goals to go through at Highbury, Arsenal suffered a setback before the match as Henry was relegated to the substitute's bench following a foot injury. It was PSV's turn to dominate the first half this time as Arsenal looked increasingly rattled.

The Gunners did receive a stroke of luck when PSV defender Alex diverted a corner into his own net in the 58th minute. The tie was level on aggregate and Arsenal turned the heat on, replacing Julio Baptista with Henry for the final 25 minutes.

Though, it was PSV who struck the fatal blow when Alex redeemed himself with a fine header from Mendez's free kick to beat Lehmann in the 83rd minute. PSV held on for the rest of normal time and injury time to progress to the quarter-finals 2-1 on aggregate at Arsenal's expense.

4. Lyon 2-1 Real Madrid: 2009-10

Miralem Pjanic's strike would eliminate Real Madrid

Miralem Pjanic's strike eliminated Real Madrid in 2009-10

Real Madrid had a torrid time in European competitions after their famous 2002 title triumph. A round of 16 elimination at the hands of Juventus in 2004-05 would start a trend of Los Blancos failing to get past the same stage for the next six years despite possessing stars like Luis Figo, Zinedine Zidane, Michael Owen and David Beckham.

By the 2009-10 season, Real had done away with the old guard while ushering in a new 'Galacticos' era with the likes Cristiano Ronaldo, Kaka, Gonzalo Higuain and Karim Benzema and were determined to break the jinx. That year saw Real drawn against French side Olympique Lyonnais at the round of 16 stage of the Champions League. The French side had just been displaced as Ligue 1 monarchs by Bordeaux after six straight titles and were a side in transition.

That did not stop Lyon from winning the first leg 1-0 at the Stade Gerland courtesy of a Jean Makoun wonder strike. Ronaldo and co. were desperate to overcome the deficit in the second leg at the Santiago Bernabeu and CR7 cancelled it out within the first six minutes.

Despite being on the backfoot for much of the opening half, Lyon had a few chances at Madrid's goal and Maxime Gonalons, Lisandro and Sidney Govou tested Casillas. Lyon were becoming increasingly confident and regained the lead in the tie with 15 minutes left.

Kim Kallstrom and Cesar Delgado sliced open the Madrid midfield and fed the Argentine Lisandro, who executed a first time lay-off that saw the ball reach Miralem Pjanic. The Bosnian beat Casillas at his near post and Real were left needing to score two more to progress.

Los Blancos could muster none and Lyon went through to the quarterfinals where they had the pleasure of eliminating domestic rivals Bordeaux to reach a first Champions League semi-final.

As for Real, that round of 16 jinx would be broken the very next year when they beat none other than Lyon 4-1 on aggregate.

3. A.S Roma 4 - 2 Real Madrid: 2007-08

Roma pulled off a great upset by beating Real Madrid in both legs at the 07-08 Champions League

Roma pulled off a great upset by beating Real Madrid over both legs in the 07-08 Champions League

Frustrated at the continued European disappointments during the Galacticos era, Real Madrid fans were relieved when they were placed against Italian giants but European minnows A.S Roma at the round of 16 stage of the 2007-08 Champions League.

Roma had never won the Champions League or the UEFA Cup and were expected to be easy pickings for Los Blancos, but the Giallorossi had steadily progressed under Luciano Spalletti over the past two years and had won the Coppa Italia the previous season. They also featured the reigning European Golden boot winner Francesco Totti in their ranks.

Real started brightly in Rome's Stadio Olimpico, racing to a 1-0 lead within the first eight minutes, but the famous 'Curva Sud' boosted the morale of the Italians and David Pizarro equalised by the 25th minute. After the break, Amantino Mancini scored to give Roma the advantage, which they protected until the final whistle.

Despite the setback, Real were still favourites to overcome the setback at the Santiago Bernabeu, considering that a 1-0 win would be enough to go through, but the one goal requirement suddenly became three as Rodrigo Taddei shocked Iker Casillas to give Roma the lead in the 73rd minute. Raul equalised minutes later, but the Romans were still ahead on aggregate.

Deep into injury time, desperate Real were further punished by a brilliant Roma counter-attack which culminated in Mirko Vucinic beating Casillas to give Roma a 2-1 win on the night and a 4-2 victory on aggregate.

It would be another three years before Real were finally able to break the 'round of 16 curse' at the Champions League.

2. Porto 3 - 2 Manchester United: 2003-04

The other dash : Costinha takes off after his injury time goal at Old Trafford
The other dash: Costinha takes off after his injury-time goal at Old Trafford2003-04 Champions League saw a certain Portuguese manager announce himself to the English footballing world with a legendary dash at Old Trafford following Costinha's last-minute equalizer that eliminated the Red Devils from the competition.

Some 15 years later, Jose Mourinho is the manager of Manchester United but the Old Trafford faithful haven't forgotten how he led F.C Porto to victory over Manchester United in the Round of 16 stage of the Champions League all that years ago.

Mourinho had just won the UEFA Cup with Porto the previous season and the grittiness of his talented side came to the fore in the first leg at the Estadio Dragao. Comprised of the likes of Ricardo Carvalho, Nuno Valente, Deco and Benni McCarthy, the Porto squad was way more than just an average side edged on by their manager.

Despite Quinton Fortune giving United an early lead, two goals from McCarthy saw Porto win the leg 2-1 over ten-men United who also had Roy Keane sent off.

United could win the tie with an unanswered single goal victory in the return leg and they seemed right on track when Paul Scholes headed in from close range to give United control in the tie on away goals.

Deep into second-half injury time, however, United keeper Tim Howard could only parry McCarthy's freekick and Costinha was the quickest to pounce on the loose ball. A second later, the ball was in the back of the net and both Costinha and Mourinho had taken off on their victorious dashes.

Porto would complete their dream run in glorious fashion, eliminating Lyon, Deportivo La Coruna and finally Monaco to become the last underdog to win the Champions League.

1. APOEL Nicosia 1-1 Lyon: 2011-12

APOEL banked on their vocifeous homesupport to beat Lyon

APOEL banked on their vociferous home support to beat Lyon

Clubs from Cyprus were traditionally associated with dismal showings in European tournaments but a change was sweeping Cypriot football towards the end of the 2000s. Anorthosis Famagusta had become the first Cypriot club to reach the Champions League Group stages in 2008-09, but it was their great rivals APOEL who would make history three years later by becoming the first club from the tiny nation to progress beyond the group stages.

Remarkably topping a group comprising of Porto and Zenit St Petersburg, APOEL were drawn to face French giants Lyon in the round of 16. A gritty showing in the first leg in France could not prevent a 1-0 reverse at the hands of Alexandre Lacazette and co, but APOEL were prepared to give their all in the return leg.

Lyon players were greeted with a huge banner at GSP Stadium that read - 'Feel the terror of Nicosia' and the stadium was a wave of orange to support the home side. Sure enough, Gustavo Manduca slotted home from close range after just nine minutes to even the score for the Cypriots.

The French side seemed unsettled amidst the hostile environment and despite a chaotic 30 minutes of extra time where APOEL found themselves reduced to ten men, Lyon couldn't find the breakthrough.

At the ensuing penalty shootouts, APOEL goalkeeper Dionisis Chiotis was the hero as he saved spot kicks from Lacazette and Michael Bastos. None of the APOEL players missed a penalty as the tie ended 4-3 to APOEL on shootouts.

The streets of Nicosia were marked with wild celebrations as the club that was founded inside a sweet shop some 90 years back became the first Cypriot club to reach the Champions League quarter-finals.

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Edited by Martin King
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