By 90Min
November 25, 2018

With the 2018/19 Champions League group stage nearing its crunch conclusion, all eyes are soon going to be on the knockout rounds as half the clubs fall out the competition.

Will the big names be crashing out and hitting the canvas unexpectedly this season?

Here's a look at nine of the most shocking UEFA Champions League knockouts in football history...


Tottenham Hotspur vs Milan (2010/11)

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Despite a relatively historic past, Tottenham were considered small fry when they entered the 2010/11 Champions League after finally finishing fourth in the Premier League.

Milan, on the other hand, had an incredible record in the competition over the previous decade and were expected to win the tie when the two clubs were paired in the last 16.

A single goal from Peter Crouch towards the end of the San Siro leg was the only one scored in the tie and proved decisive. This was the same season that a Milan side with Zlatan Ibrahimovic would go on to win Serie A - showing the level of Spurs' conquest.


Monaco vs Real Madrid (2003/04)

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Real Madrid were at the height of the Galacticos era in 2003/04. David Beckham had recently signed for the club, joining Ronaldo, Zinedine Zidane, Luis Figo, Raul and Roberto Carlos in the star studded ranks. It was a team built for one purpose: Champions League glory.

But Monaco, who had finished in the bottom half of Ligue 1 in two of the previous three seasons, had different ideas when the clubs met in the quarter finals of the competition.

Fernando Morientes, who was on loan from Real, kept Monaco alive with a consolation goal in the first leg. Trailing 4-2, the French side then won 3-1 at home - Morientes scored again - to level the aggregate scoreline at 5-5 and prevail on away goals.


Roma vs Barcelona (2017/18)

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Barcelona were cruising towards the Champions League semi finals last season in search of a first European title since 2015, but the Catalans came unstuck in the second leg of their quarter final tie with Roma.

Barça were 4-1 up from the first leg in Spain, while Roma had never previously been beyond the last eight of the competition (post-1992) and looked all but dead and buried.

Yet a sensational 3-0 win at Stadio Olimpico in the return game, sealed with a late goal from centre back Kostas Manolas, tied the aggregate score at 4-4. And by virtue of Edin Dzeko's late consolation in the first leg, Roma had done enough to knock their heavyweight opponent out.


Bayer Leverkusen vs Manchester United (2001/02)

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Manchester United manager Sir Alex Ferguson was aiming to reach the Champions League final in his home city of Glasgow in 2002. The only problem was that plucky German upstarts Bayer Leverkusen, who had already shocked Arsenal, Juventus and Liverpool, stood in the way.

Leverkusen simply refused to be beaten and equalised twice to draw the first leg of the semi final tie 2-2 at Old Trafford. They again went behind in the return leg at home and yet still found another equaliser to tie the aggregate scoreline at 3-3, putting them ahead on away goals.

United had the chance to win it through Diego Forlan in the dying minutes, only for namesake Diego Placente to heroically clear the goal-bound effort off the line.


APOEL vs Lyon (2011/12)

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For Cypriot club APOEL, simply getting to the Champions League group stage for only the second time ever was an achievement in itself in the 2011/12 campaign.

They had navigated three increasingly tough qualifying rounds and remarkably finished top of a group containing Zenit St Petersburg, Porto and Shakhtar Donetsk - all of whom had won the UEFA Cup/Europa League within the previous three years.

Lyon were APOEL's biggest scalp of all, with the seven-time French champions crumbling in the last 16 after a 1-1 aggregate scoreline eventually led to a penalty shootout. Never before or since has a Cypriot team won a Champions League knockout tie.


Dynamo Kyiv vs Real Madrid (1998/99)

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A Soviet force in the 1960s, 1970s and 1980s, Dynamo Kyiv once again started to stir with a talented generation featuring a young Andriy Shevchenko in the late 1990s, reaching the Champions League quarter finals in 1997/98.

A year later, the Ukrainians came back stronger and pulled off the unthinkable by putting reigning European champions Real Madrid to the sword, progressing to the semi finals.

Dynamo took the lead in the Bernabeu through Shevchenko, eventually drawing 1-1 in Spain. But the young forward then netted a brace in a 2-0 win in the return leg in Kyiv to unceremoniously dump holders and then seven-time champions Real out of the competition.


Porto vs Manchester United (2003/04)

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Jose Mourinho won his first European trophy in 2003 in the shape of the UEFA Cup, but his Porto side's 1-1 draw at Old Trafford in the Champions League the following season that knocked Manchester United out of the competition really put the coach on the map.

United were stunned in the first leg as Porto won 2-1 in the Estadio do Dragao, and even though the English side were on course to progress on away goals after drawing level on aggregate in the second leg at Old Trafford, a very late Costinha goal sent them crashing out.

Mourinho went running off down the Old Trafford touchline to celebrate, the legend of the 'special one' was born.


Deportivo La Coruna vs Milan (2003/04)

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Milan were arguably the most domineering team in Europe during the mid-2000s, when they reached three out of five Champions League finals, winning two of them.

So for the mighty Rossoneri to be knocked out of the competition by Deportivo La Coruna in the 2003/04 quarter finals was a shock. For it to happen when Milan held a 4-1 aggregate lead was nothing short of seismic.

Although one of the best clubs in Spain, Deportivo were still relative newcomers to Europe's top table and hammering a Milan team containing Paolo Maldini, Alessandro Nesta and Cafu by four goals to nil to overturn the aggregate deficit was completely unexpected.


Barcelona vs PSG (2016/17)

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Barcelona pulled off the unthinkable comeback during the 2016/17 Champions League campaign, knocking Paris Saint-Germain out of the competition at the last 16 stage - despite the French giants being 4-0 up on aggregate at the halfway stage of the tie.

Barça had reduced the deficit to one shortly after half-time in the return leg, but when Edinson Cavani scored for PSG it extended the lead and gave the Parisians an invaluable away goal.

By the time the tie reached the closing stages, the Catalans still had to score three goals to progress. Incredibly, they did it. Neymar scored twice in quick succession, and then Sergi Roberto became the hero in the 95th minute by making it 6-1 on the night - and 6-5 on aggregate.


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