Champions League winners tend to struggle.
For over 20 years, the Champions League was never retained. While certain top tiers across Europe became one-horse races, putting up the same level of performance in Europe had always been a completely different ball game.
It meant that a dynasty was always hard to forge. Ajax won three European Cups in the 1970s, followed by Bayern Munich; Nottingham Forest won two in a row. It was so much easier to assert your dominance as one of the great sides in history back then: the holders were the only constants in the competition, with other clubs coming and going depending on who won the league.
Not anymore. With a cast of regulars in Europe, doing well two seasons in a row has never been so difficult. Just check out the history for yourself…
1993/94 - Olympique Marseille (Did not qualify)
French domestic football would perhaps never recover from the aftermath of the country’s first - and so far only - triumph in Europe’s top competition. Marseille’s golden era was tainted by corruption, as match-fixing allegations swirled following Ligue 1 titles and a Champions League glory.
Marseille were demoted to the second division in France and chucked out of the Champions League, the first and only time that the champions did not participate in the following season of the competition.
1994/95 - AC Milan (Runners-up)
AC Milan headed into this season’s Champions League as the overwhelming favourites. They’d won the Scudetto at home scoring just 36 all goals that season but demolished Barcelona 4-0 in a Champions League final in Athens.
The following season saw the crown slip. Milan only finished fourth in Serie A and lost in the final of the Champions League to the precocious Ajax generation led by Louis van Gaal.
1995/96 - Ajax (Runners-up)
Ajax came within a whisker of retaining the Champions League in 1996. De Godenzonen were still in great form, topping a group that included Real Madrid, beating Borussia Dortmund and Panathinaikos and setting up a final against Juventus. No one, it seemed, had worked out how to defend against van Gaal’s 3-3-1-3 formation, with Jari Litmanen scoring for fun in Europe.
The Old Lady won their second title, however, beating Ajax on penalties to take Old Big Ears back to Italy once more.
1996/97 - Juventus (Runners-up)
In 1997, again, the holders got all the way to the final. If you were surprised to Juve triumph in ‘96 though, that had nothing on ‘97’s final.
Dortmund finished second in their group and squeaked past Manchester United for a first-ever final, while Juventus dispatched of Ajax again, this time in the semis and with an emphatic 4-1 second-leg victory. In the final, however, the Germans prevailed for the country’s first Champions League since reunification. Paul Lambert did quite the job on Zinedine Zidane, too.
1997/98 - Borussia Dortmund (Semi-finals)
Juventus made it three finals in a row in 1998 - though both of the 1997 finalists were knocked out by Real Madrid. Dortmund even beat Bayern Munich in the quarter-finals, but couldn’t overcome Los Blancos in the semis, losing 2-0 on aggregate.
1998/99 - Real Madrid (Quarter-finals)
It felt as if Real Madrid were back where they belonged. The Galactico era was about to take shape, with Raul, Clarence Seedorf, Roberto Carlos and Fernando Hierro the lynchpins of the side.
And they perhaps would have gone onto great things sooner, had they not have been knocked out by Dynamo Kiev in the second round. Guus Hiddink was sacked just a couple of weeks before the tie. Serves them right, Jupp Heynckes would say, for sacking him after winning the Champions League the season before.
1999/2000 - Manchester United (Quarter-finals)
Infamously, Manchester United conscientiously objected from the FA Cup after winning the Champions League. Some would say that Roy Keane and his defence did the same thing in Europe the following season.
With a quarter-final second leg against Real Madrid delicately poised, Captain Keano turned the ball into his own net before Raul was left in acres of space to take his time for the second. When Redondo backheel-chopped around Henning Berg to set up a third, United were consigned to defeat in some style. They’d lose 3-2 in the end, while Real would lift the title again in Saint-Denis, France.
2000/01 - Real Madrid (Semi-finals)
Again, the holders would be knocked out by the champions-elect in 2001. Real Madrid would make it to the semi-finals this time around, looking to set up a clash against either Valencia again or Leeds United, only for Bayern to beat them in both legs. Spare a thought for Valencia, who lost the final, again, for the second season running.
2001/02 - Bayern Munich (Quarter-finals)
Real Madrid would get their own back on Bayern Munich. It felt as if whoever was going to win out of these two was going to take home the title.
Ivan Helguera smuggled the ball into the net from a Roberto Carlos cross in the second leg, meaning that Real would advance on away goals. After taking a battering from Bayern though, Raul broke free towards the end to feed Guti for one of the biggest “limbs” moments ever in the Bernabeu. The final was all Zidane’s.
2002/03 - Real Madrid (Semi-finals)
The Galacticos had made World Cup star Ronaldo their marquee summer signing the previous summer, and the Brazilian’s hat-trick in a thrilling 4-3 defeat to Manchester United in the quarter-finals was enough to see Los Blancos through.
In the semis, Ronaldo scored again in a 2-1 first leg victory over Juventus – putting Madrid in the driving seat for a return to Old Trafford in the final.
However, goals from each of the Old Lady’s attacking trio – David Trezeguet, Alessandro Del Piero and Pavel Nedved – in Turin set up an all-Italian final instead.
2003/04 - AC Milan (Quarter-finals)
Milan breezed through their quarter-final first leg against Deportivo La Coruna 4-1, with goals from Kaka, Andriy Shevchenko and Andrea Pirlo.
With Arsenal and Real Madrid crashing out the night before the second leg fixture, the Rossoneri were essentially champions-elect, and looked set to be the first back-to-back winners of the Champions League era.
But no one told Depor. The Spanish side raced into a 3-0 first-half lead – enough to put them through with their away goal – before a 76th minute Fran strike put the tie to bed.
2004/05 - Porto (Round of 16)
Jose Mourinho left, and the backbone of the previous year’s side went too: Ricardo Carvalho, Deco, Paulo Ferreira and Carlos Alberto left Porto a weakened side.
Finishing second in the group stage to Mourinho’s Chelsea, it was a three-goal masterclass from Inter Milan’s Adriano at the San Siro that dumped them out 4-2 on aggregate in the round of 16.
2005/06 - Liverpool (Round of 16)
Liverpool’s fifth-placed Premier League finish had given UEFA a bit of a headache the previous summer, as they figured out how to squeeze five English teams into the competition.
Poor Everton limped out at the qualifying stage, while Liverpool breezed through the group stage unbeaten – only to be turned over by Benfica in both legs of the second round, losing 3-0 on aggregate.
2006/07 - Barcelona (Round of 16)
Liverpool’s journey to the final included a tense affair with Frank Rijkaard’s Barcelona. A 2-1 win at the Camp Nou, with goals from Craig Bellamy and John Arne Riise, was enough to squeeze Barca out on away goals, despite Eidur Gudjohnsen’s late strike at Anfield.
2007/08 - AC Milan (Round of 16)
For the fourth year in a row, the reigning champions couldn’t make it to the quarter-finals. A 0-0 draw in north London meant that AC Milan welcomed Arsene Wenger’s Arsenal to the San Siro knowing they needed a win to go through.
Instead, the Gunners turned in a perfect display, scoring two goals in the final 10 minutes, courtesy of Cesc Fabregas and Emmanuel Adebayor.
2008/09 - Manchester United (Runners up)
The first winners to make it all the way to final the following year in over a decade, Manchester United overcame Inter, Porto and Arsenal to set up an encounter with that Pep Guardiola Barcelona side.
A near-perfect starting XI (no offence, Sylvinho), Barca were on top of their game and looked unlikely to lose after Samuel Eto’o’s 10th minute opener. When Leo Messi peeled away from Rio Ferdinand to score a header with 20 minutes to go, United’s players looked emotionally spent.
2009/10 - Barcelona (Semi-finals)
The image of Jose Mourinho sprinting across the Camp Nou pitch, pointing to the sky, as Victor Valdes tries in vain to pull him back is one that has been seared into the very fabric of the Champions League. This was one-third of Inter’s treble under the Special One.
Barca fell at the semi-final stage, in the first of many instalments of Pep versus Jose. It became more than just a European tie, it was the battle of philosophies; the right way to play football against the dark arts, the overly complicated against a stout defensive performance. It a generation-defining clash.
2010/11 - Inter Milan (Quarter-finals)
The tie that knocked holders Inter Milan out of the 2010/11 Champions League is a strange one to look back on. Schalke won 5-2 and 2-1 respectively to reach a semi-final.
If that’s not weird enough, Raul and Joel Matip both scored, despite being from very different eras of the sport. Inter still haven’t got to the final four in the Champions League since.
2011/12 - Barcelona (Semi-finals)
After the horror of losing the 2009 semi-final to Barcelona is somewhat controversial circumstances at Stamford Bridge, Chelsea more than got their own back in 2012. Roberto Di Matteo, against all odds, denied Pep Guardiola’s last season in charge ending in a final between Barca and Bayern in the Champions League final.
When Didier Drogba’s single strike at the Bridge settled the first leg, Sergio Busquets and Andres Iniesta - the hero of three years’ prior - struck two goals to put Barca in the driving seat, only for Ramires to strike on the stroke of half-time. An away goal favoured Chelsea, who were pummelled by Pep’s side all second half.
Cue Fernando Torres, rounding the keeper with seconds to go, to secure the Blues’ second Champions League final in four years. An iconic moment in the club’s history.
2012/13 - Chelsea (Group stage)
In 2012, Chelsea made history as the first club to win the Champions League in the 21st century, having not won it in the 20th. Months later, they made more history for all the wrong reasons.
Chelsea were the first holders to fail to make it out of their group in the modern era, failing to qualify for the last-16 at Shakhtar Donetsk and Juventus’s expense. Still, at least they went and won the Europa League, that season.
2013/14 - Bayern Munich (Semi-finals)
In 2013, Robert Lewandowski scored four times in a single game for Dortmund to knock Real Madrid out of the Champions League semi-finals. Los Blancos, scarred by this, did not underestimate German opposition the following year.
Sergio Ramos and Cristiano Ronaldo both bagged braces in a second leg in Munich to see Real Madrid safely through to the final this time around.
2014/15 - Real Madrid (Semi-finals)
Just as in 2004, Real Madrid were stung by one of their own in the Champions League in 2015. Back then, it was Monaco’s Fernando Morientes, on loan from Real, scoring home and away to knock out his parent club from the competition. This time, it was Alvaro Morata.
Morata had left his boyhood club for Juventus but had a buy-back clause, which Real Madrid actually exercised after he netted against them in both legs. His away goal in the second leg ultimately became the difference, cancelling out Ronaldo’s from the first.
2015/16 - Barcelona (Quarter-finals)
Atletico Madrid may have squeaked through the round of 16 with an 8-7 penalty shootout win over PSV Eindhoven (following two goalless draws) but the quarter-final tie with previous season treble winners Barca was a different affair.
A 2-1 home win for Barcelona may have put Luis Enrique’s side in the driving side, but Atleti had that all-important away goal.
When Antoine Griezmann put them ahead before half-time in the second leg, Atletico shut up shop in true Diego Simeone style. A last-minute penalty for the French forward finished the game off, and set up an all-Madrid final...
2016/17 - Real Madrid (Winners)
Zinedine Zidane was not considered the most sophisticated of managers, and Madrid were considered by some to be something of a blunt instrument, reliant on the sheer talent of Cristiano Ronaldo.
But since the Champions League’s reinvention in the early 1990s, no side had retained the trophy until Zizou’s Madrid did.
Sweeping away Leverkusen, Guardiola’s Bayern Munich and Atletico on the way to the final, Madrid turned on the style with a 4-1 win over Juventus at the Millenium Stadium. Sophistication, schmophistication.
2017/18 - Real Madrid (Winners)
Winning the trophy twice in a row made history; winning it three times without interruption was unthinkable.
They didn’t have it easy, either: Los Blancos knocked out French champions PSG, Italian champions Juventus and German champions Bayern Munich in successive knockout stages to make it to Kiev, and a showdown with Jurgen Klopp’s Liverpool.
An injury to Mohamed Salah, a knock to Loris Karius’ noggin and an overhead kick wonder goal Gareth Bale later, and Zidane’s team were confirmed as one of Europe’s greatest ever sides.
2018/19 - Real Madrid (Round of 16)
In a shock twist, Zidane walked out of the Bernabeu in the summer of 2018. Madrid’s replacement strategy was shambolic, announcing the hiring of Spain national team coach Julien Lopetegui on the eve of the World Cup.
La Roja promptly sacked him before the tournament started, and his luck was no better in his new role: Madrid handed him his P45 in October, after a dreadful start.
Santiago Solari came in to steady the ship, until Ajax tore Madrid apart 4-1 at the Bernabeu in a brutal display that dumped them out 5-3 on aggregate. A week later, Zidane was reinstated.
2019/20 - Liverpool (Round of 16)
Liverpool had begun the season in imperious form, racing into a 13-point Premier League lead by the new year.
A 1-0 away defeat to Diego Simeone’s Atletico Madrid in February started to change things. By the time COVID put football on hiatus in mid-March, Liverpool had lost their first league game of the season (Watford, February 29), been knocked out of the FA Cup (Chelsea, March 3) and had their hopes of retaining the Champions League dashed.
Atletico bet Liverpool 3-2 after extra time in the second leg, becoming the only team to win at Anfield in a remarkable season for the Reds.
2020/21 - Bayern Munich (Quarter-finals)
Hansi Flick’s Bayern took their commanding presence into the 2020/21 season, and were many pundits’ favourites to win the Champions League again – as elite sides across Europe went through transition phases disrupted by coronavirus and a congested season. A quarter-final tie against the previous year’s beaten finalists PSG was surely an argument in their favour.
But two breathtaking legs of football left FC Hollywood going home. Goals from Kylian Mbappe and Marquinhos gave Mauricio Pochetinno’s side a 3-2 win in Munich, and refused to be cowed into a defensive approach at home.
Mbappe, Neymar and Moise Kean regularly broke free of the Germans’ high line, with the Brazilian hitting the woodwork three times to make a 1-0 Bayern win a thrilling affair.
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Conor Pope is the Online Editor of FourFourTwo, overseeing all digital content, and joined the team in February 2019. He plays football regularly, both on grass and artificial surfaces, and has a large, discerning and ever-growing collection of football shirts from around the world.
He supports Blackburn Rovers and holds a season ticket with south London non-league side Dulwich Hamlet. His main football passions include Tugay, the San Siro and only using a winter ball when it snows.
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