28. Milan v Juventus (2002/03)
Goes without saying.
27. Chelsea v Liverpool (2004/05)
This was the one where Jorge Valdano said the words ‘shit on a stick’. There was a contentious goal given in the second leg, which had a nerve-wracking ending, but doesn’t make up for an incredibly drab semi-final tie.
26. Spurs v Liverpool (2018/19)
Many are always sceptical of finals involving countries from the same nation in the Champions League. In 2019 in Madrid, Spurs and Liverpool showed why they are. There were goals in the first and last minute of normal time, but that was pretty much it, and whoever you rooted for at the Metropolitano, you were glad when it was over.
25. Chelsea v Liverpool (2006/07)
The Chelsea-Liverpool semi-final that came two years after the ghost goal may not have had the ‘s on s’ label from Valdano, but it was no thriller either. Both teams won each home leg 1-0, and the tie had to be settled on penalties. Don’t kid yourself, you don’t remember anything from it.
24. Barcelona v Real Madrid (2001/02)
Sadly for this version of El Clasico, it ranks lowly because it’s not as memorable as, either other European ties, or other games involving both teams. Also loses points thanks to Roberto Bonano ruining the aesthetics of Zinedine Zidane’s goal in the first leg.
23. Atletico Madrid v Real Madrid (2014/15)
There was a time when it seemed like the Madrid derby would be new Chelsea-Liverpool in the Champions League, as both city rivals met for four successive seasons. The second of those was the least memorable, with a drawn-out goalless stalemate at the Vicente Calderon followed by a deserved Real 1-0 win in the second leg.
22. Milan v Inter (2002/03)
Familiarity can breed a lot of things in football, and a stalemate is not unusually one of them. The Derby Della Madonnina had its place in the European sun in 2003, when both sides met in the semi-final. A goalless first leg was followed by 1-1 draw in the second leg, and because it just had to be him, Hector Cuper managed a side who got knocked out of the Champions League on away goals despite playing both games in the same stadium. If it’s any consolation, that rule no longer exists, and it wasn’t the worst all-Italian tie of that year.
21. Milan v Inter (2004/05)
Two years later, Milan and Inter would do it again, this time in the quarter-finals. This time, sparks flew, there were flares, and Milan goalkeeper Dida was hit, in a tie the Rossoneri won home and away. And who can forget that iconic Rui Costa and Marco Materazzi image. On the pitch itself? Don’t worry about it.
20. Chelsea v Man City (2020/21)
The good. In a season of eeriness, this final had fans, and UEFA chose to move the game to a location closer to the supporters of both teams. Kai Havertz scored the winner for Chelsea, and Pep Guardiola didn’t beat the overthinking mad scientist allegations. The not-so-good. Try and think of any actual highlight from the second half of this final especially.
19. Real Madrid v Valencia (1999/00)
The first of two successive Champions League final defeats for Valencia, and the second of three titles in five seasons for Real Madrid. Steve McManaman scored a neat volley, and Raul ran half the pitch to seal the game. Let’s not drag this out.
18. Barcelona v Atletico Madrid (2015/16)
Barcelona were holders of the Champions League coming into this tie, and despite conceding early, rallied to win the first leg against ten-man Atletico. It was a strenuous first leg, as well, as they dealt with an intense rearguard action before scoring twice in the second half. In the return game in the Spanish capital, the rearguard was just as tasking, but this time MSN would have no reprieve, as Atleti mounted a brilliant recovery to send Los Cules packing.
17. Barcelona v Atletico Madrid (2013/14)
But they had done battle in the same round two seasons earlier. Back in 2014, Atletico Madrid were in their first Champions League season in four years and hadn’t beaten Barcelona in five. For Diego Simeone’s side, the Champions League Last 8 was uncharted territory, fun as it had been, it was meant to end here, especially given they lost top scorer Diego Costa early in the first leg. But this was an Atleti team that had no intention of reading the script in 2013/14, as their league position would show, and after getting a 1-1 draw at the Nou Camp, came out on top in the second leg, in what you could describe as a 1-0 battering.
16. Chelsea v Manchester United (2010/11)
Chelsea vs Man United in 2011 was meant to be a repeat of the 2008 final, with the added spice of two elite managers like Sir Alex Ferguson and Carlo Ancelotti in charge of two sides who were the main title rivals in the Premier League at the time. The tie wasn’t a disappointment by any means, there’s something underwhelming about how, by the 77th minute of the second leg, it was pretty much done.
15. Real Madrid v Atletico Madrid (2016/17)
Speaking of ‘not disappointing, but done early’, step forward the latest installment of the Madrid derby in Europe. Version 4 came in the semi-final in 2017, but (no) thanks to a Cristiano Ronald hat-trick, it was all but done after the first leg. Atletico threatened a revival and drama-laden return leg in the final derby at the Vicente Calderon, scoring twice early on, but the spectre of the away goals haunted, and before half-time, Real bagged that killer strike, and we were left with 45 minutes that were basically a procession.
14. Lyon v Bordeaux (2009/10)
The only tie of this category featuring the French, and while having Lyon in the Last 8 in 2010 would be a mild surprise, Bordeaux were never meant to be here. Having been drawn in a group with Bayern Munich and Juventus, they were meant to turn up, and have a shot at a Europa League place. Instead, they qualified with two games to spare, won the group, and took 10 points from Juve and Bayern combined. Having swatted aside Olympiakos in the Last 16, they had earned the right to be favourites in the quarter-finals against Lyon. But Les Gones themselves had seen off Liverpool in the group stage, before beating Real Madrid in the first knockout round, and thanks to a Lisandro Lopez double, won this first leg 3-1. It was far from done, and back at the Chaban-Delmas, Marouane Chamakh (remember him?) gave Bordeaux the lead before half-time, halved the deficit. The home side were within one goal from going through, but Lyon would hold firm, claiming their first ever semi-final spot in the competition.
13. Real Madrid v Atletico Madrid (2015/16)
In Atletico Madrid’s quest to finally be kings of Europe, the team most in their way in recent past has been neighbours Real Madrid. And in 2016, they met for their second Champions League final clash in three years, in Milan. Sergio Ramos got the ball rolling for Real early on, before Antoine Griezmann missed a penalty early in the second half. Atletico would draw thanks to substitute Yannick Ferreira Carrasco, but as the game went to a penalty shoot-out, Los Colcheronos would suffer more continental heartbreak, losing 5-3 thanks to kicks from 12 yards.
12. Chelsea v Arsenal (2003/04)
In 2004, Arsenal had a shot at the treble, to go with an unprecedented unbeaten run in the league. And in the Champions League, they looked like they could do it, as they were in the Champions Final quarter-final alongside Monaco, Real Madrid, Deportivo, Milan, Porto and Lyon. Their opponents were Chelsea, who they’d beaten three times already that season, and a 1-1 draw at Stamford Bridge in the first leg seemed like a procession to Arsenal’s first ever semi-final spot. But despite Arsenal taking the lead in the second leg, it was Chelsea who rallied, with goals from Frank Lampard and Wayne Bridge scoring second half goals to send the Gunners crashing out of Europe.
11. Manchester United v Arsenal (2008/09)
Man United vs Arsenal wasn’t quite the classics’ classic. But this is a tie that checked the box for excitement. A ridiculous long-range free-kick. A supreme counter-attack. United ceding possession and doing for the Gunners once more. And a weird red card that denied Darren Fletcher a chance to play in the Champions League. Fun all around. Not the most memorable, but doesn’t lack re-watch quality.
10. Valencia v Barcelona (1999/00)
At the turn of the century, Valencia would make their first ever Champions League final, and they thrilled their way to the showpiece game in Paris. Los Che saw off Lazio in the quarter-final, before coming up against Barcelona in the Last 4. The first leg of the semi-final was at the Mestalla, and Valencia put up a masterpiece at home, smashing Barcelona 4-1. And despite a late rally from the Catalan side at the Nou Camp, Hector Cuper’s side coasted to the final with relative ease.
9. Liverpool v Manchester City (2017/18)
Probably the second game in the beginning… when Man City and Liverpool were about to become domestic rivals. This Champions League quarter-final came three months after a ferocious 4-3 win for the Reds in the league. In that league game at Anfield, Liverpool had a second half blitz that ultimately shattered City’s unbeaten start to the league season. Here, the blitz came earlier, with Jurgen Klopp’s side racing into a 3-0 lead before the midpoint of the first half. City had no answer, and were left with it all to do in the second leg. But despite an early goal at the Etihad, there would be no comeback, as Liverpool extinguished any hopes of that with two second half goals for a 5-1 win on aggregate.
8. Arsenal v Liverpool (2007/08)
Extra points for commentary for this tie. In April 2008, Arsenal and Liverpool met three times in eight days, and Sky’s Rob Hawthorne made references to the ‘horse’s head’ and ‘offers that can’t be refused’ as he called it the greatest trilogy since The Godfather – meanwhile, in the league meeting between both European ties, Steve Wilson referred to it as the ‘Phoney War’. On the pitch, the first leg at the Emirates produced an entertaining 1-1 draw, and it was surpassed by a classic second leg at Anfield, which had six goals, a superb solo run from Theo Walcott, a retaliatory solo move by Ryan Babel, and some weird misses.
7. Manchester United v Chelsea (2007/08)
Moscow. Draining rain. Game carried on till the next day. Red cards for silly moves. Penalty misses. That slip. A minor classic, if you can say so. Manchester United and Chelsea were tussling for the domestic title for three seasons when they met in the Champions League final in 2008, a few weeks after United had pipped Chelsea to the Premier League crown. If ever we needed a rebuttal to the argument that same-country European finals don’t hit the spot, this game was it. Yet, you could argue this was not the best the same-country Champions League final of this century to feature CR7…
6. Real Madrid v Atletico Madrid (2013/14)
…That’s because the first installment in the Madrid Derby Champions League Chronicles is, so far, the best installment. When both sides met in Lisbon in 2014, Real were chasing La Decima, and a first European crown in 12 years. Atletico, meanwhile, were looking for their very first. And boy did Los Colcheronos came mighty close. They took the lead in the first half through Diego Godin – the man who’d won them the La Liga title a few weeks earlier – and held firm against their rivals… until the 94th minute, when Sergio Ramos headed in Luka Modric’s corner. Extra-time it went to, and when Gareth Bale scored – another header – to put Real in front in the second half of the extended time, Atleti were spent. Two more Real goals came in. Real would not be denied, and for Atletico, it was a case of wondering what might have been had they simply put a man on the post for that corner.
5. Liverpool v Chelsea (2007/08)
By 2008, Liverpool and Chelsea had met for three straight Champions League seasons, and this was the scorelines of those six games after 90 minutes; 0-0, 1-0, 0-0, 0-0, 1-0, 1-0 (picture Jorge Valdano turning off the TV in disgust). When they met in the yet another semi-final in 2008, we looked to be heading for another similar score-line, as Liverpool took the lead in the first half of the first leg at Anfield through Dirk Kuyt and looked set for an advantage. In truth, it was another drab affair spurred on by tension more than anything else. But as the game entered stoppage time, John Arne Riise connived to head the ball into his own net, gifting the Chelsea an equaliser, and the first ever away goal in a tie between these two, setting up a barnstorming second leg. Five goals. A controversial disallowed goal. A controversial allowed goal. A penalty given. A penalty claim denied. Avram Grant on his knees. Two strikes from Didier Drogba earned Chelsea their first ever Champions League final place, and the first time they’d vanquished Liverpool on the continental front. It wouldn’t be the last.
4. Bayern Munich v Dortmund (2012/13)
2012/13 was a statement season for German frontrunners Borussia Dortmund and Bayern Munich in Europe. Particularly in the semi-finals, where they met the leading Spanish giants in Real Madrid and Barcelona. Dortmund may have survived the second leg against Real Madrid by a hair’s breadth, but they, and Robert Lewandowski, had put on a masterclass in the first leg to all but finish the tie. Bayern Munich, meanwhile coasted even more against Barcelona, romping to a 7-0 aggregate win, both results signalling, not quite era changes, but tactical evolutions in the modern game.
3. Spurs v Manchester City (2018/19)
When Spurs hosted Man City in the Champions League quarter-final first leg in 2019, they hadn’t beaten the English champions in four games, conceding 10 goals in that period, and their league form was starting to fall off a cliff, marking the start of the end for Mauricio Pochettino. So, City would be favourites, right? Well, Spurs were diverting all their energy towards their European adventures, and despite conceding an early penalty at their then-newly renovated home ground, would muster a clean sheet in a gritty 1-0 win in the first leg. But the tie was far from done, and if Spurs knew it, they really knew it when they conceded very early on in the second leg. Yet, by the 9th minute of the return fixture at the Etihad, they were 3-1 up on aggregate, thanks to a Heung-Min Son double. City would fight back, in an incredible first half, going into the break 3-2 ahead, and only behind on away goals. Then when Sergio Aguero thumped Pep Guardiola’s team in front in the second half, that looked to be that. Except not, as Fernando Llorente would give Spurs another say, with a goal that spurred multiple tweaks to the handball rule into action. City then thought they’d won it in stoppage thanks to Raheem Sterling, only for VAR to erase that moment of euphoria and plunge Pep to his knees. Spurs had been creating a habit of surviving in that Champions League season by the finest of margins, and they did again… and there was more to come.
2. Liverpool v Chelsea (2008/09)
The latest installment in the Liverpool vs Chelsea Champions League Tales happened 14 years ago. Those heady days look gone now, but they did serve us a classic for the memories. Almost like they knew it won’t happen for a while to come, and to repay us for those early 1-0s and 0-0s, Liverpool and Chelsea played out an incredible game in the first leg at Anfield, with Chelsea winning 3-1. Yet the events of the second leg made sure the first wouldn’t linger in the memory. Liverpool needed to score three without reply at Stamford Bridge to go through, and astonishingly, before the half-hour mark in the second leg, the Reds were 2-0 up in West London. Suddenly, only the tiny fabric of the away goal protected Chelsea’s lead. Yet, less than 15 minutes into the second half, Chelsea were back level on the night, and had their two-goal aggregate lead restored. And when Frank Lampard made it 6-3 on aggregate with less than 15 minutes to play, that was that, right? Wrong! Seven minutes later Liverpool were 4-3 up on the night, and 6-3 became 6-5. Now it was the Reds who had more away goals, and one more would take them to the semis, against the odds. But Lampard would have the final say in an absurd night. ‘This was a Champions League tie played not by modern millionaire footballers but by maniacs with what appeared to be a mutual desire to push the self-destruct button’, said Matt Lawton of the Daily Mail.
1. Real Madrid v Barcelona (2010/11)
Real Madrid. Barcelona. April. 2011. Four games. 19 days. Pep Guardiola. Jose Mourinho. It was the height of the Catalan-Madrid Footballing Cold War. Real and Barca were going to meet four times in 19 days. The first of those were in the league; Real and Barca drew, there was a red card, and Barcelona basically sealed La Liga. It was big, but we can let it slide. The second of those was the Spanish Cup final; Real won 1-0, Mourinho’s first trophy with the club, there was a red card, and Sergio Ramos damaged the cup. It was big, and a trophy was at stake, but that’s by the by. The third of those was a European Cup semi-final first leg. There was a red card, and another…. And then another. There was a breathtaking Lionel Messi goal. There were shoves, kicks, dives, faints, falls, cries, newspaper tussles, conspiracy theories, and borderline death threats. It wasn’t just the events on the pitch that mark this tie out. It’s the fact that it aged Jose Mourinho and had a long-lasting impact on the Portuguese. It exhausted Pep Guardiola and ultimately aided his departure from the Nou Camp a year earlier. It fostered division in the Spanish squad, spurred that Graham Hunter book, and that Stadio episode. Words flew as much as tackles, and there were more punditry takes than goals. And, whether we want to admit it or not, it took a bit out of us two. It was the best we could get, but, please, never again.
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