UEFA Champions League: The Top 10 Semi-finals of this Century

It’s the ‘toughest game of the season’, Arsene Wenger called it. Well, technically, Wenger was more specific towards the second leg of the semi-final of the Champions League, but that should also imply that it makes the whole semi-final of the Champions League the toughest games of the season.

And that’s where we currently are in the 2024/25 season. We began proper with 36, it didn’t really get straightforward until we got to 16, and now there are four. Arsenal, Inter, Paris St. Germain, and Barcelona all step out in the penultimate phase of Europe’s top club competition, seeking a path to glory.

Before that, though, they’ll have to serve four combined semi-final matches. Whether they’ll go down in history and be memorable remains to be seen.

But what are the best Champions League semi-finals of this century?

10. Bayern Munich v Real Madrid (2011/12) 

From the get-go in the 2011/12 season, Bayern Munich had a primary goal; reach that home Champions League final. Bavaria would be hosting the party of the glory game of that European season, and Die Roten wanted to be in attendance, and not just usher in the guests.

They’d made their way to the Last 4, and in the other corner was Real Madrid, under Jose Mourinho, who themselves faced the prospect of a Clasico final with bitter rivals Barcelona. The first leg, in Munich, saw Bayern leave it late to grab a deserved 2-1 win against Real. 

But 15 minutes into the second leg at the Bernabeu, Real looked to be running away with the semi-final; a Cristiano Ronaldo double meant they were out in front in the tie, and closing in on that final (albeit, at that point, the possibility of a Clasico showpiece game was no longer). Arjen Robben delivered a needed riposte for the Germans, and no further goals meant a 3-3 aggregate score... and penalties.

Bayern must have been certain fortune was smiling on them when Real’s first two takers – seasoned pros in Ronaldo and Kaka – saw their efforts saved, and although Real skipper and goalie Iker Casillas dragged the hosts into it with successive saves of his own, a Sergio Ramos howler put the visitors in match point. Bastian Schweinsteiger would convert, and whatever supplication Mourinho was making on the touchline proved fruitless, as Real would be reduced to agony on their own patch. 

9. Barcelona v Chelsea (2008/09)

When spring of 2009 rolled around, Pep Guardiola had hair, and was a rookie manager. Also, Barcelona and Chelsea would be meeting in the Champions League for the fourth time in five seasons. In that time, they’d traded knockout blows, Camp Nou stalemates, and group stage conflicts.

The 2009 semi-final was the most advanced they’d ever met in the competition, and they duelled to another Camp Nou stalemate in the first leg, in a game where the headline was Barcelona failing to score at home for the first (and only) time that season.

And nine minutes into the second leg, the Catalans were in trouble, as an absolute worldie of goal by Michael Essien gave Chelsea the lead at Stamford Bridge. The game would be dominated by (and remembered for) Chelsea being denied different penalty claims by Norwegian referee Tom Henning Ovrebo, but in terms of both sides, it was by the Blues, whose directness Barca found too much to handle, and when that led to Eric Abidal getting sent off for the visitors midway through the second half, things looked all but done.

Barcelona hadn’t managed a single shot all game and looked bereft of ideas as the game entered stoppage time, until a tired Essien clearance gave Lionel Messi room. One pass to Andres Iniesta and one stunning shot into the top corner later, Pep was running manically down the Stamford Bridge touchline, Michael Ballack would be remembered for chasing after the ref, and Didier Drogba earned himself a three-match ban by speaking to the camera. Barca, though, were off to Rome, to kickstart an era of dominance.

8. Borussia Dortmund v Real Madrid (2012/13) 

For the select few who were not surprised by how Real Madrid’s Remontada preview before getting them dumped by Arsenal this season was a bit much, this tie was probably why. By 2013, it was 15 years since Borussia Dortmund reached the semi-final stage of the Champions League. Back then, in the 1997/98 season, their journey was ended by Real Madrid, whom they faced again. Real were making a third successive Last 4 appearance, and despite having failed to beat Dortmund when they met in the group phase of the same season (a draw and a defeat, as they finished in second place to the German champions), were favourites in this semi-final (and like the previous season, could potentially have a Clasico final with Barcelona).

But Robert Lewandowski had other ideas, especially in the first leg. The Pole gave Dortmund a deserved lead, and despite a Real Madrid goal against the run of play taking both teams level into the break, bagged three more, writing his name all over the tie, as Dortmund planted one foot in a Wembley final.

Ahead of the second leg, there would be articles and official club videos from Real Madrid, appealing to the Bernabeu crowd to come in their droves and help pull off the thing. A fire-cracking start led to missed chances, particularly from Mesut Ozil and Gonzalo Higuain, while, in the second half, they had goalkeeper Diego Lopez to thank for denying Lewandowski and Ilkay Gundogan.

A late rally would be spurred by Karim Benzema and Sergio Ramos, as both scored in the final 10 minutes to leave Real on the cusp of the improbable, but Dortmund held firm, leaving Los Blancos with a third successive semi-final exit.

7. Chelsea v Liverpool (2007/08) 

If Chelsea and Barcelona met with regularity in the 2000s in the Champions League, then Chelsea and Liverpool took it to another level, one not even the frequent Real Madrid v Man City match-ups of recent can match. Between the 2004/05 and 2008/09 season, both sides made sure to meet every campaign.

But if the meetings were regular, they were far from exciting. The six matches of first three seasons produced three goals in total, with three goalless draws and disdain from Jorge Valdano. In no time in those meetings had an away team scored, or had there been a goal after halftime, and three goals were all in 1-0 wins.

So, there wasn’t exactly much expectation in terms of excitement when they met in the spring of 2008, a third semi-final clash between the pair in four seasons. This was the first meeting in that time without Jose Mourinho, who’d left Chelsea back in September 2007, but it looked to be business as usual in the first leg, when Dirk Kuyt gave Liverpool the lead at Anfield, and chances were very few and very far between. Everyone was prepared to tick off another 1-0 home win, when, in the final minute, Salomon Kalou sent a hopefully cross into the Liverpool box, and John Arne Riise contrived to head into his own goal. A huge shock to the Chelsea-Liverpool status quo, and an away goal advantage to the Blues, who’d lost the previous semi-final ties against the Reds.

That late goal seemed to open the floodgates in the second leg, as the goals poured in at the Bridge. Chelsea took the lead through Didier Drogba, before Fernando Torres levelled for Liverpool in the second half, forcing extra-time. In the extra 30 minutes, Chelsea saw a Michael Essien goal disallowed for offside, Liverpool’s Sami Hyypia gave away a penalty that Frank Lampard converted, and when Drogba made it 4-2 on aggregate on the cusp of halftime in extra-time, that looked to be that. But Liverpool still had room to rev up a nervy ending, thanks to Ryan Babel. Chelsea would hold on, though, for a first ever Champions League final, as both waited to do battle in the competition again the next year.

6. Real Madrid v Manchester City (2021/22) 

The new Chelsea-Liverpool? Real Madrid and Man City have met in the knockout phase of five of the past six Champions League seasons, but their meeting in the 2021/22 season – the first of a four in a row – may well be the most epic... so far.

In the 2021/22, ahead of their semi-final clash, Real Madrid had just about scaled fences on their way to this round. They were outplayed in the first leg defeat of their Last 16 tie against PSG, and looked to be heading out when they were 2-0 down on aggregate midway through the second half of the return leg, until a Karim Benzema hat-trick helped pull off a miracle. Meanwhile, in the quarter-final, despite taking 3-1 first leg lead against Chelsea (in a rather even game) to the Bernabeu, they saw that lead vanish on home turf, and with less than 10 minutes left, were 4-3 down on aggregate. That was until a Rodrygo effort forced extra-time, and Benzema (who scored a hat-trick in the first leg this time) headed in a 5-4 aggregate winner.

So, when they went 2-0 down against Man City less than 15 minutes into the first leg of the semis, surely this was where they’d be exposed, and their luck would run out. City would miss chances from Riyad Mahrez and Phil Foden to extend that advantage even further, before Benzema once again pulled the rabbit out of the hat to reduce the arrears. It was City who won the first leg at the Etihad, but every time they looked to be pulling clear, Real would drag themselves back into the picture, and a 4-3 defeat was more than Los Blancos deserved. “We left them alive”, City boss Pep Guardiola said after the first leg.

But when, in the return leg, Mahrez put City 5-3 up on aggregate with less than 20 minutes, and when they took that two-goal advantage into stoppage time at the Bernabeu, surely this was it. Real Madrid were surely not dragging themselves back into the picture. Except they were, as two goals in less than two minutes – both from Rodrygo – had Real back from the dead again. “They prayed for miracles, and miracles arrived”, exclaimed Peter Drury in the commentary box. “You just can’t knock them out, Real Madrid” was Martin Tyler’s line. Once again, we headed for extra-time, and once again, it would be Benzema to deliver the death blow. City left Real alive, and paid the price.

5. Inter v Barcelona (2009/10) 

The name ‘Eyjafjallajökull’ could lay claim to be the most crucial one in football in 2010. Rumour has it the volcanic eruptions in that part of Iceland were the reason we didn’t get the words ‘Blackburn Rovers forward Robert Lewandowski’, and then there was the Champions League semis, where Barcelona had to take a train ride to Italy ahead of their first leg clash against Inter. The Catalans, holders of the Champions League title, did take the lead in at the San Siro, but Inter hit back with three goals, to take massive 3-1 lead to the Camp Nou.

If eruptions dominated the first leg, the second was largely about being watertight. Inter – Jose Mourinho’s Inter – would be reduced to 10 men after Sergio Busquets exaggerated Thiago Motta’s contact, and immediately set out to barricade their goal. They'd reportedly give the ball away on purpose to avoid losing their shape, which would explain why their only shot of the game came from the halfway line from Cristian Chivu, and looked more like a fair play pass to restart the game, and put on an incredible rearguard action against the most fearsome side in Europe at the time.

Barca did pull a goal back thanks to Gerard Pique, but was one not enough, and it would be Inter who’d make the final, their first in 43 years. Cue Mourinho running around the Camp Nou after fulltime in triumph and vengeance (having been passed up for the Barca job two years earlier); his actions earning the Camp Nou sprinklers early activity, and ultimately him the Real Madrid job... and maybe another place in this list.

4. Chelsea v Barcelona (2011/12) 

After the madness of not facing each other in any of the two seasons after the 2009 semi-final, Chelsea and Barcelona got paired up in another Last 4 tie, three years later. The picture was different this time; Chelsea were not as formidable as they were in ‘09, languishing in 6th in the Premier League and saving their season with cup runs, while Barcelona were the subject of debate as to whether they’re greatest side of all time.

That pretty much highlighted the disparity between both sides, and why Chelsea set up rearguard action in the first leg at Stamford Bridge. Well, it worked, as the Blues snatched a goal from nowhere on the cusp of halftime, and held on to that for the entire first leg, as Barcelona hit bar, post, man on the line, and everywhere but the Chelsea net.

But the tie looked to be running away from Chelsea when Barcelona scored twice in the first half of the second leg, two goals in eight minutes either side of Blues captain John Terry getting sent off. Yet, under Roberto Di Matteo, Chelsea had shown an ability to respond to adversity and strike when collapse seemed inevitable, and through Ramires, they did that before the break. Suddenly, the Blues had gone from the verge of fading away to leading on away goals. Like the first leg, Barcelona would hit bar, post, and anywhere but the Chelsea net in the second half, and in the final minutes of added time, Fernando Torres would be through on the Barcelona goal. Cue the Gary Neville moan, and the rest was improbable history.

3. Liverpool v Barcelona (2018/19) 

It’s testament to Barcelona’s consistency that they pretty much dominate this semi-final list, but that’s scant consolation when they remember this particular lie. In the two seasons prior to 2018/19, Barcelona featured in some of the most historically absurd Champions League ties. In 2017, they overturned a 4-0 aggregate deficit to beat PSG 6-5 in the Last 16, while the following season they were victims of an absurd Roma comeback in the quarter-final.

So, they knew a 3-0 lead against Liverpool in the first leg at Camp Nou wasn’t quite a sign of the tie being done and dusted. Luis Suarez and a double from Lionel Messi had given them a healthy advantage, but even Messi figured it wasn’t done, as his reaction to a late Ousmane Dembele miss from the first leg showed.

Liverpool were without talisman Mohammed Salah for the return leg at Anfield, but they took the lead inside six minutes via Divock Origi. But Barcelona surely knew an onslaught was coming, and had learned lessons from their collapse in Rome a year earlier, right? Even the Barcelona Twitter admin was quite certain they’d at least score once and avoid another catastrophe. But when Georginio Wijnaldum reduced the deficit for Liverpool to 3-2 in the 54th minute, Barca had little time to panic before Wijnaldum struck again less than 180 seconds later. Another three-goal lead was gone, and a raucous Anfield wasn’t the best place for such generosity. Then with 12 minutes left, Liverpool had a corner...

2. Tottenham v Ajax (2018/19) 

Liverpool’s miracle comeback against Barcelona is one for ages. Yet, one could argue it wasn’t even the best comeback of that 48-hour period. Enter Tottenham v Ajax. 

Spurs had beaten Dortmund comprehensively in the Last 16, but that was an outlier in their Champions League campaign that season. In the group stage, they just about scraped past Inter to finish second (behind Barcelona), and in the quarter-final, away goals, the handball debate, and VAR dominated as they narrowly slipped past Man City. Ajax, meanwhile, had statement wins at the Bernabeu and at the Juventus Stadium in successive knockout rounds.

So, when a Donny van de Beek goal gave Erik Ten Hag’s youthful Dutch side a rather straightforward win at Spurs in the first leg, it looked like little much was on. It looked even more so when Ajax raced into the 2-0 lead in the second leg thanks to Matthijs de Ligt and Hakim Ziyech. Spurs had a handful of moments, but never looked like they were onto much in the tie.

Yet, the second half of the second leg didn’t clock 15 minutes when Lucas Moura scored twice to get us to 3-2 on aggregate. Suddenly, Spurs sensed the impossible, upped the risk-o-metre, and a youthful Ajax panicked, leading to early defensive changes from Ten Hag in bringing in Joel Veltman and Daley Sinkgraven. Yet, Ajax managed to reassert themselves, and close shaves from Ziyech kept Spurs alive in the tie.

Mauricio Pochettino’s side were playing more with desperation and urgency than a plan, and it started to look like a killer Ajax goal was more on than a Spurs winner. But in the fifth minute of stoppage time, Moussa Sissoko launched one forward; and a Fernando Llorente duel and Dele Alli pass later, Lucas Moura was completing his hat-trick, stunning the Johan Cruyff Arena, reducing Spurs and Ajax fans/players to tears, for different emotions.

1. Real Madrid v Barcelona (2010/11) 

'We had the intention to keep the game at 0-0, then bring on a striker, then a third phase with a No. 10 behind three forwards. But the ref didn't allow it.'' Jose Mourinho, 2011. 

Yes, really. This is the No 1 Champions League semi-final of this century.

Not so much for on-pitch quality (though that wasn’t lacking), but rather for everything surrounding it. It was part of the 4-games-in-19-days episode of El Clasico. It was the height of Pep v Mourinho tussle, so much so that the former finally went all out in press conference. There were strained friendships, red cards, conspiracy theories, touchline squabbles, mass viewings, podcast episodes, long reads, and books.

For a few years in the 2010s, there was the prospect of a Clasico final in the Champions League. That never materialised, and this was the next best thing. Or the next worst, depending on how you look at it.

When Barcelona walked into the Bernabeu 14 years ago this week, the first of the four Clasicos had pretty much settled La Liga, and the second had decided the winners of the Spanish Cup. So, the final two was for a chance at Wembley (and according to many, a certainty of Wembley glory) in the Champions League final.

Did Real stifle Barca? Yes! Was the Bernabeu a cacophony? Yes! Was a player sent off? Yes! Was another sent off on the sidelines? Yes! Did Mourinho talk himself into a dismissal? Yes! Did Messi settle this tie with pure brilliance? Yes!

Were there finger-pointing and conspiracy theories after? Yes! Is this the best semi-final of this century? Yes! Are we glad Real and Barca haven’t met in the competition since? Yes!