Chelsea could be seen as something of a Johnny-come-lately when it comes to major football honours. Of their top flight titles, five have been won since 2004, and six of their eight FA Cups have been won since 2000. It’s a similar story in Europe, with their two Champions Leagues and two Europa Leagues coming from 2012 onwards. To be fair, they won a couple of Cup Winners’ Cups in the 20th century. In this article, though, we’ll be focussing on Chelsea’s successes and failures in the Champions League and its forerunner, the European Cup.
Interestingly, Chelsea qualified for the inaugural European Cup after winning the Division One title in the 1954/55 season. Alas, the Football League urged them to withdraw and their first chance at European glory was halted before it really began (we’ll go into more detail about that later in the article).
When Did Chelsea Last Win the Champions League?
Chelsea last won the Champions League at the end of the 2020/21 season when they beat fellow Premier League side, Manchester City, 1-0 in the final. It took place at the Estádio do Dragão in Porto in front of just 14,110 fans (which was reduced due to the global health crisis at the time). German attacking midfielder, Kai Havertz, scored the only goal of the game. It was the second time they had won the tournament having also triumphed in 2012.
Champions League Finals
As well as winning the Champions League twice, Chelsea also made it to the final in 2008 when they lost to Manchester United on penalties (more on that major disappointment later). Winning two out of three finals isn’t a bad return, and their pair of victories puts them in joint-ninth position on the all-time list, level with Juventus, Benfica, Nottingham Forest and Porto. Interestingly, there is quite a contrast between these double UCL winning sides, with Juventus making nine finals and Porto and Forest just two!
|2012||Bayern Munich||Won||1-1 (AET and 4-3 on penalties)|
|2008||Manchester United||Lost||1-1 (AET and 6-5 on penalties)|
Stage of Elimination
Chelsea have competed in the Champions League 18 times, and all of those were in the Champions League rather than the European Cup (as it was known before the 1992/93 season). Of those 18 attempts to conquer Europe, they’ve only failed to make it past the Group Stage of the tournament once, back in 2012/13 (more of that below).
|Stage||Number of Times||Percentage|
|Round of 16||6||33%|
Note that the information provided is correct at the start of the 2022/23 season. Note also that the percentages are rounded and hence do not total 100%.
Times Chelsea Won the Champions League
Here we’ll outline how Chelsea won the Champions League in 2012 and 2021, with both games needing extra time and penalties.
2021 – Blues Out-Battle Pep’s City
Both Chelsea and Man City certainly deserved to be in the 2021 Champions League final. Pep’s City had overcome Borussia Dortmund in the quarters and PSG in the semis. More pertinently for us, Thomas Tuchel’s Blues had got the better of Atletico, Porto and Real Madrid on their journey to the final in Porto. Going into the game, City were the strong favourites with bookies, pundits and neutrals alike. Many people thought it was ‘Pep’s time’ to lead his Man City team to European glory and finally lift another Champions League. Chelsea, of course, had other ideas.
Played in front of a reduced crowd, the final wasn’t overly high on quality as Chelsea successfully nullified many of City’s attacking options. Out-muscling their opponents and defending deeply, Chelsea limited the opportunities for City and managed to carve out a crucial goal just before half time when Kai Havertz rounded Ederson after a Mason Mount through ball.
After the break, City weren’t exactly brimming with attacking ideas and the injury in the second half to Kevin De Bruyne didn’t help their cause. Even the introduction of Sergio Aguero for his last game for City couldn’t change things and Chelsea battled their way to their second Champions League triumph against the odds.
2012 – Drogba Leads Charge for Glory
Former Chelsea player, Roberto Di Matteo, had only been in the manager’s role for a couple of months when his side were suddenly facing Bayern Munich in the Champions League final… in Munich! Di Matteo had been installed as caretaker boss when Andre Villas-Boas was sacked in March 2012, seemingly – at least in part – due to the Blues losing their Round of 16 first leg match at Napoli 3-1. Whether the trigger-happy board thought their side had no chance of progressing after that, or it was a master stroke to motivate the team to achieve something remarkable, we don’t know. What we do know is that Chelsea won the second leg 4-1 after extra time to sneak through to the quarters.
They won home and away against Benfica to set up a mouth-watering tie against Barcelona in the semis. A disciplined and assured display say Chelsea earn a 1-0 home win in the first leg, Didier Drogba scoring the only goal of the game. It was a little less assured in the second leg in Catalonia, but Chelsea came back from 2-0 down to draw 2-2 and book their place in the final.
As with their final in 2021, Chelsea went into the game as underdogs, not least because Munich were playing on their own patch. But on the night there was not much to pick between the sides and it looked as though the match might end goalless. That is until Thomas Müller put Bayern into the lead in the 83rd minute. There seemed insufficient time for Chelsea to respond against a side, managed by Jupp Heynckes, who were rather stubborn defensively. But Didier Drogba pounced on a Juan Mata corner and headed in the equaliser.
There were no further goals in extra time and, just like when Chelsea lost against Man United in 2008, the Champions League would be decided on spot-kicks. Penalties against a German side don’t usually end well, but this time around it was the English team who prevailed thanks to missed kicks from Ivica Olic and the usually rock-solid Bastian Schweinsteiger. Guess who nailed the winning spot-kick for the Blue? Yep, that man Didier Drogba.
Chelsea’s Worst Upsets
Although Chelsea have only won the tournament twice, they haven’t completely capitulated many times and so they don’t have as many disappointments as some teams. Having said that, there have been a couple of occasions that Chelsea fans won’t want to be reminded about (so look away now, Blues fans).
Group Stage Failure – 2012/13
The only time Chelsea have played in the Champions League but failed to make it out of the group was in the 2012/13 season when they went into the tournament as defending champions. They were drawn into a relatively straightforward group too, alongside Italian giants Juventus (fair enough, never an easy nut to crack), Ukrainian side, Shakhtar Donetsk, and Danish minnows, FC Nordsjælland.
With former Chelsea player, Roberto Di Matteo, in the manager’s hot seat after leading his side to European glory just a few months earlier, the Blues were very much expected to progress. But things didn’t go to plan this time around. The west Londoners started very well in their opening group game when they hosted Juventus and put themselves 2-0 up after around half an hour of the match. Unfortunately, they let the lead slip and the game ended 2-2.
The Blues followed up with a convincing 4-0 drubbing of Nordsjælland but then, disappointingly, lost 2-1 when travelling to Donetsk. They got their revenge when Shakhtar visited Stamford Bridge as the Blues ran out 3-2 victors. They then suffered a comprehensive 3-0 defeat to Juve in Turin. That cost Di Matteo his job and by the time Chelsea hammered Nordsjælland 6-1, former Liverpool boss, Rafael Benitez, was in charge. But, as it turned out, their results were only good enough to finish level on points with Shakhtar, who progressed ahead of Chelsea because of the better head-to-head away goals record!
Captain Fantastic Fluffs It Up – 2008
When it comes to Champions League disappointments, it’s hard to top Chelsea’s 2008 defeat to Manchester United in the final in Moscow. With John Terry of all people messing up royally! Chelsea had made it to the semi finals in three of the previous four years in the Champions League and they felt in a strong position to go all the way in 2008. They’d beaten another English club, Liverpool, in the semis (4-3 on aggregate) and had a team that was packed with top-class players. As well as English stars, John Terry, Frank Lampard and Ashley Cole, others in the starting line-up for the final included Dider Drogba, Michael Ballack, Claude Makelele and Michael Essien. Chelsea were formidable, with a spine of warriors and leaders that was very hard to beat.
Having said that, Man United had their fair share of stars too, with their much-vaunted front three of Wayne Rooney, Carlos Tevez and Cristiano Ronaldo all starting for the Red Devils. With so much attacking talent on the pitch, it was perhaps surprising that there were only two goals scored in 120 minutes of football. Ronaldo got the first just before the half hour, while Lampard equalised on the stroke of half time.
As always, penalties can prove something of a lottery. And, the unexpected certainly happened when none other than Ronaldo missed his spot-kick to give Chelsea fans plenty of hope that it was finally their year. (Well, to be fair to Ronnie Cech saved it… with his face!). Everyone else scored and up stepped Mr Reliable himself, club legend John Terry, to stroke in the winning penalty and lead his side to European glory… except he misread the script and promptly slipped as he took his kick and ballooned it onto the post! Nani, Anderson and Ryan Giggs scored their pens before Nicolas Anelka’s weak attempt was saved by Edwin van der Sar and Chelsea had to wait a while longer for their first taste of Champions League glory.
Barca Blow Blues Away – 2000
When Chelsea were drawn against Barcelona in the quarter finals of the 1999/2000 Champions League it looked a big ask to find a way past the Catalan stars. But then Chelsea put in a blinding performance in the first leg at Stamford Bridge, a goal from Gianfranco Zola and a brace from Tore Andre Flo earning the home side a precious 3-1 victory. All they had to do in the second leg at Camp Nou was avoid a battering. Alas, things went badly wrong for the Blues.
The Barcelona team included some truly world-class players including Rivaldo, Pep Guardiola, Luis Figo and Patrick Kluivert. It was Rivaldo who opened the scoring for the home side on 24 minutes before Portuguese legend Figo soon doubled the lead. Chelsea got one back through Flo on the hour mark and thus put themselves in the box seat once again. Unfortunately for Chelsea, Dani Garcia popped up with less than 10 minutes to go to make it 3-1 and take it to extra time.
Chelsea were still very much in it and a goal for them would have all-but clinched it. Instead, Barca’s class shone through and goals from Rivaldo and Kluivert made it 5-1 on the night, Chelsea’s worst Champions League defeat (although 6-4 on aggregate doesn’t look quite so bad). That turned out to be Barca’s high point of the tournament, however: they went down 5-3 in on aggregate in the semis to Valencia and then had to stomach bitter watching rivals Real Madrid ease to their eighth Champions League/European Cup.
Missed Opportunity in the First European Cup? – 1955/56
We’ll never know what might have happened if Chelsea had participated in the first European Cup in the 1955/56 season. They could have become the first English champions of Europe more than a decade before Manchester United achieved that feat. Alas, we’ll never know. Chelsea qualified for the inaugural tournament after winning the First Division the season before (when they finished four points clear of the chasing trio of Wolves, Portsmouth and Sunderland). Chelsea even agreed to take part in the European Cup and were lined up to played Djurgården of Sweden (a very winnable tie, in anyone’s eyes).
As it was, the football league urged Chelsea to withdraw from the tournament, which they promptly did, leaving Polish side Gwardia Warszawa to take their spot. Real Madrid started as they meant to go on Europe and promptly won the tournament after beating Reims 4-3 in the final in Paris. Though there’s no reason to think Chelsea would have gone all the way and got the better of a star-studded Madrid side, there’s always that nagging question… what if?