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Five of the Champions League’s biggest knockout round upsets

Atalanta’s maiden venture into the Champions League ended in heartbreaking fashion with a late defeat to Paris Saint-Germain this week, the first-time qualifiers coming ever so close to an upset against one of European football’s leading sides.

The Italian outfit led until the final minute of the contest before conceding two late goals in a dramatic conclusion, their giant-killing hopes ended by Eric Maxim Choupo-Moting’s stoppage-time winner.

Following Atalanta’s valiant performance against PSG, we’ve decided to look back at some of the most memorable shocks from the tournament’s latter stages, here are five of the Champions League’s biggest knockout round upsets:

Dynamo Kiev v Real Madrid – (1998/99)

The late nineties saw the emergence of an exciting Dynamo Kyiv side under the guidance of the legendary Valeriy Lobanovskyi, now in his third spell at Dynamo and boasting a team spearheaded by the talents of Andriy Shevchenko and Serhiy Rebrov.

Dynamo had made headlines with their impressive victories over Barcelona the previous season but were still ranked as outsiders heading into their quarter-final clash with Real Madrid in 1998/99, the Spanish giants having ended a 32-year wait for European Cup success the previous season.

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The first leg in Madrid saw Dynamo make a statement of intent by securing a 1-1 draw, Shevchenko scoring an opener for the visitors before Predrag Mijatović levelled the scores ahead of the return fixture.

There was no such recovery for the holders in the second leg, however, as Shevchenko scored twice to seal the Ukrainian’s passage to the last four, Dynamo sending shockwaves through Europe by eliminating the champions as they progressed to a semi-final meeting with Bayern Munich.

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Manchester United v Porto – (2003/04)

The sliding doors moment in the career of a man who would become known as the ‘Special One’, Jose Mourinho’s Porto made headlines by knocking out perennial contenders Manchester United in 2003/04.

Mourinho had impressed since taking charge of Porto and had guided the club to UEFA Cup success the previous season, but the Portuguese side were far from fancied as they returned to Europe’s elite.

Porto finished as runners-up to Real Madrid in the group stages and were subsequently handed a last-16 meeting with Premier League giants United, a side which had reached at least the quarter-finals in each of the past seven seasons.

Mourinho’s side gave themselves a chance of progress as Benni McCarthy’s brace sealed a 2-1 comeback victory in the first leg in Portugal, though their slender advantage was wiped out by Paul Scholes’ goal in the return fixture at Old Trafford.

Heading towards an exit on away goals, Costinha reacted first to Tim Howard’s spill of a stoppage-time free-kick, sparking Mourinho’s now iconic touchline sprint celebration and setting underdogs Porto on their way to becoming champions of Europe.

Deportivo v AC Milan (2003/04)

AC Milan were crowned as champions of Europe under the guidance of Carlo Ancelotti the previous season, Andriy Shevchenko’s penalty sealing shoot-out success over Juventus in the first ever all-Italian final.

The following season saw the Rossoneri once again ranked amongst the leading contenders and they reached the quarter-finals amid minimum fuss, finishing top of a straightforward group before dispatching Sparta Prague in the last-16.

Standing in Milan’s way in their bid to become the first side to defend the trophy in the Champions League era were Deportivo La Coruna, regulars in continental competition but a side who had never progressed beyond the last eight.

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The first leg saw the champions assert their dominance in formidable style, overcoming an early setback to run out convincing 4-1 winners in Milan, Walter Pandiani’s opener cancelled out by a brace from Kaka and further goals from Andriy Shevchenko and Andrea Pirlo.

Milan’s stellar cast of stars were expected to breeze into the last eight, but an early goal laid the foundations for one of the Champions League’s greatest comebacks. Pandiani’s early opener saw Deportivo surge forward with renewed belief, the Spaniard’s incredibly ahead on aggregate before half-time courtesy of strikes from Juan Carlos Valeron and Albert Luque.

Fran scored a fourth to cap an incredible evening and send Deportivo through to the last four, though their run would be ended by eventual winners Porto in the semi-finals.

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APOEL v Lyon (2011/12)

The Champions League can often appear a closed shop with latter stages largely dominated by sides from Europe’s major leagues, but the 2011/12 campaign saw minnows Apoel Nicosia make their mark on continental competition.

Cypriot football ranks some way below the leading leagues of England, Italy and Spain, but Apoel showed their ability to punch above their weight with a run to the last eight of the Champions League.

After topping a group including the likes of Zenit St Petersburg and two-time winners Porto, Apoel were drawn to face French side Lyon, regulars in the Champions League and a side which had won seven consecutive Ligue titles between 2002 and 2008.

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Alexandre Lacazette’s goal handed Lyon a 1-0 advantage to take to Cyprus for the return fixture, where a resilient Apoel levelled the contest through an early goal from Gustavo Manduca. The two teams could not be separated following 210 minutes of action over two legs, though it was Apoel who advanced following a 4-2 penalty shoot-out success.

Their victory booked a dream date with Real Madrid in the last eight for a club whose transfer record stood at just £800,000, though their run was ended in emphatic fashion following an 8-2 aggregate defeat.

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Ajax v Real Madrid (2018/19)

The most recent inclusion on this list came from last season’s competition, Ajax stunning holders Real Madrid with a display of breathtaking attacking football.

Ajax have a long an illustrious history in European competition but the financial disparity between Dutch football and Europe’s major leagues means there hopes of success are built on clever recruitment and nurturing homegrown talent.

Drawn to face the reigning champions and record 13-time winners in the last-16, Ajax’s European venture looked all but over following a 2-1 first leg defeat in Amsterdam, Marco Asensio’s late goal giving Real an advantage ahead of the return in Spain.

Ajax’s exciting and fearless young side had other ideas, however, and produced a scintillating display of attacking football at the Bernabeu, running out 4-1 victors with Dusan Tadic starring – becoming just the ninth player in history to receive a 10/10 rating from French publication L’Equipe.

The win saw Ajax progress from a knockout round tie for the first time in 22 years and eliminated a side which had won four of the past five editions of the Champions League, a sensational display from a side who represented a breath of fresh air on the often predictable European stage last season.

Read – Five of the best individual performances in Champions League history

Read Also – Ranking the five goalkeepers with most clean sheets in Champions League history

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