Man City, Man Utd and Liverpool feature among ten greatest knockout ties in Champions League history

Matt Stead

Nothing complicated here: just ten of the greatest two-legged ties in Champions League history, with the obvious and necessary apology for not including that one you like.


10) Borussia Dortmund 3 Malaga 2 (2013 quarter-final)
If you’re only ever going to get one crack at the European Cup, you might as well make it a stone-cold classic run that ends in a blaze of glory. Malaga may return to the Champions League stage again some day but that halcyon era under Manuel Pellegrini could not seem further from reality for a side currently facing relegation to Spain’s third tier.

Los Boquerones received their invite by pipping Atletico Madrid to fourth place in La Liga in 2012, with top scorer Salomon Rondon and creative lynchpin Santi Cazorla leaving that same summer. Isco shouldered the responsibility while Manchester City loanee Roque Santa Cruz helped atone for a loss of goals. Malaga maintained their solid domestic form but it came at no expense to their European excursions.

Their reward for navigating an unbeaten group stage and a last-16 meeting with Porto was a showdown against Jurgen Klopp and Borussia Dortmund. The Germans were dominant in the first leg at La Rosaleda but failed to make it count with an away goal, with Mario Gotze particularly profligate. That left the second leg balanced just well enough for either side to believe they had a chance: Dortmund were at home but Malaga knew one away goal could sway it.

That came through Joaquin as early as the 25th minute, cancelled out by Robert Lewandowski just before half-time. Already heading through, Malaga solidified their place in the semi-finals as Eliseu scored with eight minutes to go. Yet Marco Reus and an incredibly offside Felipe Santana struck in injury time to swing the tie between two future Premier League-winning managers completely. Thankfully Pellegrini doesn’t still hold a grudge.


9) Dynamo Kyiv 3 Real Madrid 1 (1999 quarter-final)
That there was none of the typical hysteria from the Spanish media at holders Real Madrid being dumped out of the 1999 Champions League by relative novices was testament to two things: their misfortune over two legs and the burgeoning brilliance of a Dynamo Kyiv team that had been threatening to sweep the continent for a year or so.

Valery Lobanovsky has guided the Ukrainians to the quarter-finals in 1998, thrashing Barcelona 7-0 on aggregate in the group stage before falling to Juventus at the first knockout hurdle. That imbued Andriy Shevchenko, Serhiy Rebrov, Oleg Luzhny and friends with the requisite experience to cruise through a group containing Arsenal the following season, before the draw pitted them against John Toshack’s reigning champions.

Shevchenko, who the club had fought so hard to keep the previous summer, put the visitors ahead in the first leg at the Bernabeu before Predrag Mijatovic levelled a few minutes later with a sublime free-kick. Nothing could separate the two sides heading into the return fixture a fortnight later, when a 22-year-old Shevchenko netted twice again to underline his excellence. ‘The best don’t always win,’ wrote the editor of Spanish newspaper AS, while Marca declared: ‘The champions were the best and leave the Cup with their heads held high.’


8) Bayer Leverkusen 4 Liverpool 3 (2002 quarter-final)
It remains to be seen whether the world is ready to accommodate a Champions League knockout game between Liverpool and Manchester United: the social-media implosion; the debate over whose magical European nights could beat up the other’s magical European nights; the longreads about Gabriel Heinze. They met in the Europa League in 2016 but came so close to arranging the first all-English European Cup meeting in 24 years more than a decade prior.

Leverkusen, as it happened, would eliminate both in successive rounds before suffering one of the most pronounced collapses in football history. Klaus Toppmoller’s wonderful side dumped Liverpool out in the quarter-finals and dispatched Manchester United in the semis before losing to Real Madrid in their second final in four days, having also missed out on the Bundesliga title by a single point.

Those games against Liverpool were the highlight, a 1-0 defeat at Anfield thanks to Sami Hyypia’s goal laying the groundwork for some second-leg shenanigans at the BayArena. Michael Ballack brought the hosts level on aggregate. Abel Xavier gave the visitors a vital lead. Ballack and Dimitar Berbatov scored in four second-half minutes to turn the tie. Jari Litmanen put Liverpool ahead on away goals with 11 minutes remaining. And then Lucio sprang the offside trap to lash one in past Jerzy Dudek for the victory and bring 180 quality minutes to a definitive close.


7) Manchester City 6 Monaco 6 (2017 last 16)
The inevitable issue with many knockout games is that they become cagey and cautious, both sides setting up conservatively for fear of handing the opponent a crucial advantage. Risk rarely outweighs reward. Then Manchester City and Monaco come along with a 12-goal extravaganza between a side that simply could not defend and another that chose not to.

First came a 5-3 home win at the Etihad, which featured a couple of strikes from Radamel Falcao either side of Kylian Mbappe’s first Champions League goal. Monaco led for 28 minutes but contrived to lose by two to a Manchester City team that was in front for just 19. But the pending Ligue Un champions were sensational in the second leg as Mbappe, Fabinho and Tiemoue Bakayoko rendered Leroy Sane’s effort obsolete, Pep Guardiola left to rue his decision to play Fernandinho as the sole central midfielder behind an attacking quintet despite boasting a two-goal advantage against a free-scoring team with nothing to lose. He doesn’t half choose his moments.


6) Liverpool 4 Barcelona 3 (2019 semi-final)
There is a case to be made for the 2018/19 Champions League knockout stage being the greatest in the competition’s history. It contained Ajax’s glorious embarrassment of riches, putting paid to Real Madrid and Juventus in consecutive rounds before themselves falling to Tottenham in a sensationally dramatic semi-final. The Old Lady only reached the quarter-finals after Cristiano Ronaldo continued his personal hex over Atletico Madrid with a hat-trick to turn a 2-0 first-leg deficit to a 3-2 aggregate win. Manchester United also stormed Paris in that remarkable game, but Liverpool outdid everyone in heeding Mo Salah’s pre-match T-shirt and never giving up.

The Egyptian’s injury coincided with the absence of Roberto Firmino as Liverpool were tasked with coming from three goals down to vanquish Barcelona in the semi-finals. Anfield was rocking out of habit more than expectation but once Divock Origi scored in the seventh minute, the mood perceptibly changed. It was still not until Georginio Wijnaldum’s half-time introduction for Andy Robertson – this generation’s Didi Hamann for Steve Finnan – that Barcelona realised their fate. Ten minutes later the Dutchman had scored twice, leaving Origi, Trent Alexander-Arnold and an eager ball boy to do the rest and send Liverpool through. Ousmane Dembele and that first-leg miss still have a lot to answer for after letting Lionel Messi’s hat-trick majesty go to waste.


5) Ajax 4 Atletico Madrid 3 (1997 quarter-final)
Not until he wished to express to Mike Dean his thoughts on a perceived Alexis Sanchez dive almost a decade later had Louis van Gaal ever been so animated. Ajax, tournament winners in 1995 and runners-up in 1996, were in the 1997 semi-finals after edging past Atletico Madrid in extra-time.

That Van Gaal would be heading to La Liga himself that summer emphasised how his sensational Ajax team had come to their natural end by this point, but one final hurrah in Amsterdam was a fitting tribute. Frank Rijkaard, Edgar Davids, Finidi George, Nwankwo Kanu and Clarence Seedorf had all gone but much of their nucleus remained: Patrick Kluivert cancelled out Juan Esnaider’s early goal in the first leg before Ronald de Boer and Kiko traded efforts over 90 minutes back in Holland. Harry Redknapp’s best friend Dani struck, only for a Milinko Pantic penalty to give Atletico renewed hope and a quarter of an hour to avoid exiting on away goals. As they pushed forward for a decisive third, Tijani Babangida led and eventually converted a breakaway before leaping into the arms of his manager.


4) Manchester City 4 Tottenham 4 (2019 quarter-final)
Don’t worry: mention of this one was omitted from 6) for a reason. What transpired over two legs between a pair of familiar foes still beggars belief to this day, and not just because it featured Tottenham at the sharp end of the Champions League.

Tottenham were always second favourites to advance against the Premier League champions, who had won their last three meetings in a row and were inches ahead of Liverpool in their quest to retain their domestic crown. So when Harry Kane was substituted after less than an hour of a tense first leg, all hope seemed to have been lost. Yet Heung-min Son handed them the most slender of leads to protect at the Etihad.

Manchester City scrubbed that out within four minutes through Raheem Sterling, only for Son to net twice in response. Bernardo Silva then equalised immediately, followed by another Sterling strike to bring the aggregate score from 0-1 to 3-3 after 21 second-leg minutes. The situation settled a little thereafter until Sergio Aguero sparked it back into life on the hour, then Fernando Llorente’s arm hair nudged Tottenham ahead again with 17 minutes to play. Sterling thought he had put City through in the third minute of stoppage time yet his effort was ruled out for offside by VAR when it was still a bit of a novelty and added to the emotion rather than fuelling Peter Walton’s plans for world domination. It was pure Gazprom and Ajax would soon discover Spurs were nowhere near finished with their nonsense. Alas, come the final, they had no more nonsense to give.


3) Manchester United 2 Real Madrid 3 (2000 quarter-final)
Some might prefer the 2003 basketball extravaganza – Chelsea supporters certainly should – but that was a one-sided exhibition and almost a secondary plot line to David Beckham’s future at the time, save for the tremendous Ronaldo story arc. What occurred a few years earlier was at least closer in terms of result and intrigue, although Real Madrid were once again far superior to Manchester United.

They really shouldn’t have been. United were reigning European champions defending their Premier League crown with consummate ease, while Real spent most of the 1999/2000 season mired in a UEFA Cup qualification battle with Zaragoza, Alaves and Celta Vigo. But one team was painfully overawed by the other.

“In the first game we had too much respect for the name Real Madrid,” substitute goalkeeper Raimond van der Gouw noted after watching Mark Bosnich preserve a goalless draw from the sidelines. Only he, Roy Keane and Ryan Giggs really turned up in the Bernabeu as Andy Cole spurned one glorious headed chance and Dwight Yorke had an effort ruled out for offside.

United still felt they were in control of the tie for two reasons: Home advantage at Old Trafford; and their simple refusal to ever be beaten. They came from behind to win or draw six of their 11 Champions League games in 1998/99 and carried that belief forward. Real would crush it. Vicente Del Bosque lined them up in a 3-3-2-2 formation in which the underrated Fernando Redondo positively thrived, before he dug into Sir Alex Ferguson’s “tactical anarchy” after a chastening victory. Real took a three-goal lead after 52 minutes and to United’s credit it was whittled down to one with a sensational David Beckham effort and a Paul Scholes penalty, leaving them two minutes and stoppage-time to score twice more and advance. Even for them it was a hurdle too far.


2) Barcelona 2 Inter Milan 3 (2010 semi-final)
The bare statistics are amazing: 20 shots to one, a 94% pass-success rate against a 54% pass-success rate, 17 dribbles to four and 76% possession against a side reduced to ten men for more than an hour. Jose Mourinho lost the battle but irrefutably won the war, and he wanted to make sure the Nou Camp knew it.

Inter Milan’s heroic defensive performance in the second leg of their 2010 semi-final against Barcelona obscures the havoc they wreaked initially. Diego Milito was in inspired form at the San Siro as he assisted both Wesley Sneijder and Maicon before scoring himself to make it 3-1 in a counter-attacking first-leg masterclass.

Both that and what immediately followed remains arguably Jose Mourinho’s greatest career achievement. Lifting the trophy with Porto was exceptional but stopping arguably the greatest club team ever, his nemeses, winning three in a row was the realisation of his purest form.


1) Chelsea 5 Barcelona 4 (2005 last 16)
Mourinho himself might argue that point. The translator could well hold even more dear his first meeting with Barcelona in 2005, which included the very best and the very, very worst of his brand of coaching.

“Frank Rijkaard’s history as a player can’t be compared with my history as his is fantastic and mine is zero,” he noted on the eve of Chelsea’s last-16 tie against the Catalans in his first season as manager at Stamford Bridge. “As a manager though, my history cannot be compared to his. He has zero titles and I have a lot of them. I have to defend what is mine and the Champions League is mine.”

The Portuguese was singularly determined to win Europe’s premier competition for the second season in a row after his triumph with Porto. With a nine-point lead atop the Premier League table at the time of the first leg, he and Chelsea could dedicate themselves completely to Rijkaard’s Barca with no distractions.

A Juliano Belletti own goal handed them the perfect start at the Nou Camp but a questionable Didier Drogba red card altered the tie and, unfortunately, the career of Anders Frisk. He announced his immediate retirement from the game three weeks later after receiving death threats when Mourinho accused him and Rijkaard of meeting in the referee’s dressing room at half-time.

Barca compounded their one-man advantage with two goals to carry a 2-1 lead into Stamford Bridge’s second leg. It was there that the feast of football materialised: Eidur Gudjohnsen, Frank Lampard and Damien Duff stunned the Spaniards with three goals in 19 minutes to wipe out their lead. Ronaldinho scored a penalty soon after and the most iconic toe poke in history in the 38th minute to edge them ahead on away goals. But John Terry rose highest from a corner, the captain planting a glorious header past Victor Valdes with a quarter of an hour remaining to put Chelsea into the quarter-finals.

Mourinho, not for the last time, would race onto the pitch and show Barca just what it truly meant to him as Clive Tyldesley questioned who could possibly stop them. Liverpool had some ideas in mind.