Despite the two Premier League titles, domestic dominance and having one of the most enviable squads in the world, Manchester City still haven't made it past the quarter-finals in the Champions League since Pep Guardiola joined the club.
This time around, Guardiola's side aren't the underdogs anymore: the Eastlands outfit are the bookies' favourites to win the tournament. Another failure to do so and they could find themselves in the history books as one of the best teams to never lift those famous looping handles.
CHAMPIONS LEAGUE How likely are Manchester City to win the quadruple?
Of course City aren't the only great side from history to have failed to win the Champions League...
1. Arsenal, 2003/04
The Invincibles have gone down in Premier League folklore thanks to their extraordinary unbeaten feat, as a Thierry Henry-inspired team brushed aside the competition in England.
It was therefore tinged with regret when their European aspirations were ended by a familiar opponent – a Chelsea team they'd already beaten three times in other competitions during the same campaign.
A 3-0 defeat to Inter Milan at Highbury in their group opener was the worst possible start, and was followed by a draw at Lokomotiv Moscow and defeat away to Dynamo Kiev. Qualification hopes appeared to be slim, but three wins in a row – including a superb 5-1 thrashing of Inter at San Siro – sealed their passage to the knockout stages as group winners.
A 5-2 aggregate win over Celta Vigo in the last 16 set up a quarter-final for Arsenal against the Blues. A 1-1 first-leg draw at Stamford Bridge put the Gunners in pole position, extending Arsenal’s unbeaten run against their London rivals to 17 games – but Arsene Wenger’s side crashed out with a 2-1 defeat at Highbury, having led 1-0 at the break. Wayne Bridge’s 87th-minute winner still hurts in north London.
2. Chelsea, 2004/05
Jose Mourinho’s impact at Chelsea was immediate and significant. The Portuguese arrived with a burgeoning reputation, having secured an unlikely Champions League title at Porto the season prior, but he couldn’t replicate the feat for his new team despite record-breaking results on the home front. The Blues’ 95-point haul was the highest ever for a single season at the time, and was accompanied by more records: fewest goals conceded (15), most wins (29), most away wins (15), and most clean sheets kept (25) in a single campaign.
Things started promisingly in Europe as Chelsea topped a group featuring PSG, CSKA Moscow and Mourinho’s former side Porto, losing just once on the final day when top spot was already assured.
But they didn’t benefit from easy draws, and faced Ronaldinho’s Barcelona in the last 16. Nevertheless, the Spaniards were beaten 5-4 on aggregate after a classic 4-2 win at Stamford Bridge sealed by a John Terry header. Bayern Munich fell next in another thriller that finished 6-5 to the Blues on aggregate, but their journey ended in the semi-finals thanks to Luis Garcia’s ‘ghost goal’ for Liverpool which gave the Reds a 1-0 aggregate win three minutes into the second leg at Anfield.
Speaking to FourFourTwo, Garcia revealed that Mourinho still hasn’t forgotten the controversial incident. “He is still seething,” said the Spaniard. “He’ll always deny my goal, but if I was him I’d do the same."
3. Juventus, 1996-99
It’s easy to see why Juventus fans might be forgiven for thinking their side is cursed in Champions League finals. Twice they battled all the way to the end with a fine team, and twice they fell.
It’s arguably unfair to include a side that did win the Champions League just a year before these events (in 1995/96), but their individual talent, domestic dominance in an era when Serie A was Europe’s strongest league, and the fact they were on the brink of conquering Ol’ Big Ears for three seasons running merits their inclusion.
The 1997 final defeat to Borussia Dortmund remains one of the tournament’s great shock results, as the German side secured their one and only title against an Old Lady line-up featuring the likes of Zinedine Zidane, Christian Vieri and Didier Deschamps. Marcello Lippi’s side battled all the way through the competition again a year later, but this time were undone by a Predrag Mijatovic goal against Real Madrid in the Amsterdam final – their third consecutive appearance in the fixture.
On that day, Alessandro Del Piero and Pippo Inzaghi lined up in front of Zidane, while Edgar Davids had been added to the midfield. Despite boasting a squad that read like a Who’s Who of ‘90s superstars, Juve – after losing to Manchester United in the 1999 semi-finals too – had to settle for just the one European title in that decade. Since then, the Italians have made it to three more finals, losing all of them. Can Cristiano help end the curse? Well, not this year, he can't...
4. Atletico Madrid, 2013/14 and 2015/16
Diego Simeone has revolutionised Atletico Madrid since his arrival as manager in December 2011. Picking up a side that had finished seventh in La Liga and been knocked out of the Europa League group stage the season before, the fiery Argentine transformed his team into Spanish winners and serious Champions League contenders.
In 2013/14, Atleti were crowned victors of La Liga and made it all the way to the Champions League final, where they were seconds away from defeating rivals Real Madrid. Instead, they leaked a last-minute equaliser and fell to a demoralising 4-1 loss in extra-time.
Simeone’s side proved their success wasn’t a flash in the pan by getting another crack at the trophy two years later, again against their city neighbours. Again, though, heartbreak followed as Los Colchoneros lost on penalties. They did at least claim a sliver of revenge by claiming the UEFA Super Cup with a 4-2 win over Real Madrid in 2018, having scooped the Europa League title that year. Simeone hasn’t given up on his Champions League dream yet.
5. Valencia, 1999-2001
Another side to have had more than one bite at the cherry without success, Valencia’s memorable team of the millennium era came agonisingly close to European glory.
Hector Cuper’s side embarked on a spectacular run to the final, getting through two group stages before knocking out an all-star Lazio side that went on to win Serie A that year, as well as domestic rivals Barcelona. Both ties were settled thanks to superb performances at the Mestalla, but Los Che couldn’t raise their game to defeat Real Madrid at the Stade de France in Paris and slumped to a 3-0 defeat.
Captain Gaizka Mendieta inspired the Spanish side all the way from qualifiers to the final once again a year later, knocking out English sides Arsenal and Leeds en route in the quarter and semi-finals respectively.
Mendieta’s penalty gave them an early lead against Bayern Munich in the final, but Stefan Effenberg equalised from the spot. The Germans went on to triumph 5-4 in sudden death of the eventual shootout. It wasn’t all doom and gloom, though: Rafael Benitez’s arrival the following season sparked a charge to the La Liga title.
6. Inter Milan, 1998/99
While Inter Milan's great historic rivals Juventus may hold bigger regrets about their underachievement on the continent in the late ‘90s, Inter possessed a side capable of far more than they achieved. What’s more, the Nerazzurri were led by arguably the greatest player of the age, Ronaldo.
The Brazilian hit a stunning spree of form in the 1997/98 campaign, scoring 34 goals in all competitions as Inter finished runners-up in Serie A and won the UEFA Cup. Making an impact in the Champions League was the logical next step for Gigi Simoni’s side, but things soon fell apart in a disastrous campaign at San Siro.
The club went through four coaches in one season: Simoni, Mircea Lucescu, Luciano Castellini and finally Roy Hodgson, and plummeted to an eighth-placed league finish. The spotlight was turned towards their reliance on Ronaldo, who was hindered by injury problems that restricted him to just 19 league appearances all season (and yet he still finished as the club’s top scorer with 15 goals).
Inter’s return to Europe’s top competition for the first time in nine years started reasonably well, with Lucescu securing passage to the knockout stages after Simoni was sacked in November. Their group stage results had included a 3-1 victory over Real Madrid, but Dwight Yorke’s double for Manchester United in the quarter-final first leg made progression unlikely, and Inter could only muster a 1-1 draw in Milan in the return tussle.
Lucescu was duly dismissed after failing to bring out the best from a squad boasting talent that went beyond the stellar abilities of Ronaldo – Roberto Baggio, Javier Zanetti, Diego Simeone and a young Andrea Pirlo were among the stars in their ranks that year.
7. Borussia Dortmund, 2012/2013
Before Jurgen Klopp rolled into town, the spectacular 1997 Champions League triumph was by far and away the highlight of Dortmund’s European history. However, the affable German brought the club back to continental prominence with his iconic high-energy gegenpressing system which yielded impressive results and thrilled neutrals.
Klopp had established Dortmund as a major force before their run to the final in 2012/13, leading them to back-to-back Bundesliga titles. Drawn in a tough group with Manchester City, Ajax and Real Madrid, the Germans topped it without losing a game, beating both Spanish and English clubs along the way.
Shakhtar Donetsk and Malaga duly fell in the knockout stages – the latter in stunning, last-gasp circumstances – before Dortmund came face-to-face with Real Madrid again for a place in the final. A memorable 4-1 victory at Signal Iduna Park, in which Robert Lewandowski scored all four goals, ended the contest before Madrid’s 2-0 second-leg win.
Klopp’s side had the chance to assert their dominance over Bayern Munich in the first ever all-German final, but it wasn’t to be: a motivated Bayern team that had lost two finals in three years ensured there would be no agony this time with a 2-1 victory at Wembley, courtesy of Arjen Robben’s late goal.
8. Barcelona, 1993-96
The dawning of the Champions League era in 1992/93 prompted a dry spell for one of the greatest minds the game has ever seen: Johan Cruyff. The legendary Dutchman’s Barcelona team lifted the last ever European Cup in 1991/92, but couldn’t repeat the feat once the newly-branded tournament kicked off.
Cruyff’s side became known as the ‘Dream Team’ as they won four consecutive league titles between 1991 and 1994, as well as securing the 1989 Cup Winners’ Cup and aforementioned ’92 European Cup title – the club’s first.
The Dutchman left far more behind him than just trophies at Barcelona, though: his ethos is still imprinted on the club – particularly at La Masia – today. Cruyff also won 11 trophies, which made him the club’s most successful coach until a certain Pep Guardiola came along.
Despite that, his record in the Champions League was a disappointment given the riches at his disposal. Knocked out by CSKA Moscow in the second round of the competition’s inaugural season, Barça were then hammered 4-0 by AC Milan in the 1994 final despite fielding a team packing the punch of Romario, Hristo Stoichkov and Ronald Koeman. The Catalans were then defeated by PSG in the quarter-finals the following year, before failing to even qualify in Cruyff’s final season in charge.
9. Juventus, 2014-19
Over five years in Turin, Massimiliano Allegri turned Juventus into a winning machine. Building on the foundations laid by Antonio Conte, the tactician delivered a league and cup double every season at the club. But one major objective remained unachieved.
For all the positivity regarding Juve’s domestic dominance – which even Napoli’s club record 91-point tally couldn’t halt in 2018 – there is no ignoring their desperation to end a two-decade wait for another Champions League success.
Two finals came and went under Allegri’s watch, ending in defeat to Barcelona (2015) and Real Madrid (2017). Either version of the Old Lady would have been a worthy winner: the first built around the guile of Andrea Pirlo, dynamism of Paul Pogba and explosiveness of Carlos Tevez; the second featuring the much-heralded ‘BBC’ defensive unit of Andrea Barzagli, Leonardo Bonucci and Giorgio Chiellini, who supported a new-look frontline of Paulo Dybala, Gonzalo Higuain and Mario Mandzukic.
The signing of Cristiano Ronaldo in 2018 heralded perhaps Juve's best shot at the big prize but after dragging his new team into the quarter-finals via a hat-trick against Atletico, Ajax ended Allegri's search for continent glory in Turin in 2019. The Allegri era ended with Maurizio Sarri being brought in - and one of the all-time great Juventus sides fizzled out without a European trophy to show for their efforts.
10. Ajax, 1995-97
Louis van Gaal brought Ajax back to prominence in the mid-90s with a side nurturing the best young Dutch talent. It looked like his team were heading towards a period of dominance when they secured the club’s first title of the Champions League era in 1994/95 – the first time Ajax had been crowned Europe’s best since winning three consecutive European Cups in the Total Football halcyon days of the early 1970s.
What transpired can hardly be labelled as a disappointment, but it’s hard to shake the feeling that Ajax’s teams of the following two years could have – and perhaps should have – added another continental trophy to the cabinet.
The Dutch giants made it to the final again in 1995/96, where they were defeated on penalties by Juventus. Edgar Davids, Edwin van der Sar, Patrick Kluivert and the De Boer twins were among the players in red and white to play that day. Juve were their conquerors again a year later, this time in the semi-finals, where Van Gaal’s side were beaten 6-2 on aggregate in his final season at the Amsterdam club.
Subscribe to FourFourTwo today and get three issues delivered for just £3.
Thank you for reading 5 articles this month* Join now for unlimited access
Enjoy your first month for just £1 / $1 / €1
*Read 5 free articles per month without a subscription
Join now for unlimited access
Try first month for just £1 / $1 / €1
Alasdair Mackenzie is a freelance journalist based in Rome, and a FourFourTwo contributor since 2015. When not pulling on the FFT shirt, he can be found at Reuters, The Times and the i. An Italophile since growing up on a diet of Football Italia on Channel 4, he now counts himself among thousands of fans sharing a passion for Ross County and Lazio.