When it comes to European football, there is no competition better than the Champions League. Chelsea’s relationship with it has been mixed over the years, thanks in no small part to the fact that they didn’t even get to play in the competition until the 1999-2000 season. That is in spite of the fact that they were invited to take part in the inaugural version of the European Cup, which was the Champions League’s predecessor, but were asked not to by the Football Association. They won the competition for the first time in 2012, with Roberto Di Matteo at the helm.
The club would regularly reach the knockout stages of the Champions League for a time, even adding a second win in the competition in 2021 in unlikely circumstances. At the time, football was played behind closed doors due to the global health situation, with the opposition being Pep Guardiola’s all-conquering Manchester City side. Chelsea won out under the management of Thomas Tuchel, who was sacked as manager a little over a year later to prove that not even winning the biggest prize in club football is enough to protect managers from losing their jobs.
| Season | Chelsea Result | Winner | Runner Up |
|---|---|---|---|
| 2022-2023 | Quarter-Finals | Manchester City | Inter Milan |
| 2021-2022 | Quarter-Finals | Real Madrid | Liverpool |
| 2020-2021 | Winners | Chelsea | Manchester City |
| 2019-2020 | Round of 16 | Bayern Munich | Paris Saint-Germain |
| 2017-2018 | Round of 16 | Real Madrid | Liverpool |
| 2015-2016 | Round of 16 | Real Madrid | Atlético Madrid |
| 2014-2015 | Round of 16 | Barcelona | Juventus |
| 2013-2014 | Semi-Finals | Real Madrid | Atlético Madrid |
| 2012-2013 | Group Stage | Bayern Munich | Borussia Dortmund |
| 2011-2012 | Winner | Chelsea | Bayern Munich |
| 2010-2011 | Quarter-Finals | Barcelona | Manchester United |
| 2009-2010 | Round of 16 | Inter Milan | Bayern Munich |
| 2008-2009 | Semi-Finals | Barcelona | Manchester United |
| 2007-2008 | Runners-Up | Manchester United | Chelsea |
| 2006-2007 | Semi-Finals | AC Milan | Liverpool |
| 2005-2006 | Round of 16 | Barcelona | Arsenal |
| 2004-2005 | Semi-Finals | Liverpool | AC Milan |
| 2003-2004 | Semi-Finals | FC Porto | AS Monaco |
| 1999-2000 | Quarter-Finals | Real Madrid | Valencia |
Chelsea Champions League Wins
2020-2021: Manchester City 0-1 Chelsea
Group Stage
It is fair to say that the 2020-2021 Champions League campaign was one of the oddest that there has ever been, entirely owing to the way that football responded to the global health crisis of the time. Chelsea were drawn into Group E with Sevilla, Krasnodar and Rennes, being considered one of the favourites from the outset.
That favourites tag was put under immediate pressure when the Blues drew 0-0 with Sevilla in the opening group game. A 4-0 win away to Krasnodar game in the second game week, whilst a 3-0 win over Rennes in game week three helped the club further. A 2-1 win away from home against Rennes all but secured the club's progress, which was confirmed thanks to a 4-0 win away in Seville.
Chelsea progressed at the top of the group thanks to a 1-1 draw at Stamford Bridge against Krasnodar on the final game week of the group stage.
Knockout Rounds
Chelsea were drawn to face Atlético Madrid in the Round of 16, with the Spanish side hosting the Blues on the 23rd of February for the first-leg. That ended 1-0 to Chelsea, meaning that the English side was in a commanding position heading into the second-leg back at Stamford Bridge.
When Chelsea won that 2-0 thanks to goals from Hakim Ziyech and Emerson, adding to the one scored by Olivier Giroud in Spain, it meant that the Blues were through to the quarter-finals. That pitted Chelsea up against Porto, the club that former manager José Mourinho left to join the Premier League side back in 2004.
The first-leg took place in Portugal, with goals from Mason Mount and Ben Chilwell putting the Blues in a commanding position. The second-leg remained 0-0 until second-half stoppage time, with Taremi getting what turned out to be a consolation goal for Port in the 94th minute.
The semi-final was a tough draw for Chelsea, having to take on Spanish giants Real Madrid. The first-leg was a tight affair, with Christian Pulisic opening the scoring before Karim Benzema equalised. It stayed that way for the return leg, in which Timo Werner scored the opening goal and Mason Mount secured the club's place in the final in the 85th minute.
Final
It was English champions Manchester City that Chelsea faced in the final, with Pep Guardiola's team looking to finally add the trophy that the owners had craved since taking over the club to the trophy cabinet. That might well have been the case, but the Mancunian club didn't allow for Chelsea's determination to succeed.
In what was a relatively tight affair, Kai Havertz managed to break the deadlock at the Estádio do Dragão. He had been played in by Mason Mount, with the German taking on Ederson in a one-on-one. The 'keeper rushed out and got a touch, but it wasn't enough and Havertz was able to roll the ball into an empty net and hand Chelsea the club's second Champions League title.
2011-2012: Chelsea 1-1 Bayern Munich (4-3 Pens)
Group Stage
Drawn in a tough-looking Group E with Bayer Leverkusen, Valencia and Genk, Andre Villas-Boas’ side made a great start by beating the German side 2-0 at the Bridge before a draw at Valencia and an easy 5-0 win against Genk put the Blues in a commanding position at the half-way point of the group stages.
Things were in the balance after a draw at Genk and a 2-1 defeat at Leverkusen, but a dominant 3-0 win against Valencia got the job done on match day 6 to put Chelsea in the last 16 as group winners.
Knockout Rounds
Chelsea were drawn against Napoli in the round of 16 and it looked to be all over after a damaging 3-1 defeat in the first leg in Italy, the club then dispensing with Villas-Boas as manager. However, in winning by the same score at the Bridge the Blues took the tie to extra-time during which Branislav Ivanovic scored a crucial late goal to put his side into the quarter-finals.
With Roberto Di Matteo now in charge, a 1-0 win at Benfica had Chelsea fans dreaming, and a semi-final place was confirmed at Stamford Bridge when after a late Raul Meireles goal the home side won 2-1 on the night and 3-1 on aggregate to book a place against the almighty Barcelona in the last four.
Didier Drogba scored the only goal of the game in the first leg of the Champions League semi-final at home, the 1-0 scoreline looking incredibly vulnerable against a Barcelona outfit so goal-happy at the Camp Nou.
Indeed, in the second leg Barca went 2-0 up before half-time and looked to have ended Chelsea’s dream run, but a late first half goal from Ramires gave the side hope and a stoppage time equaliser on the night from Fernando Torres had the travelling fans in raptures as Chelsea reached the Champions League final for just the second time.
Final
In the final Chelsea were made to feel like the away side given that the game was played at the Allianz Arena, home of the opposition Bayern Munich, and when after a tight affair Bayern scored with just seven minutes to play it really did seem to be all over for Chelsea. Not so!
With two minutes left on the clock, club legend Didier Drogba powered home a header from a corner to send the final into extra-time. No more goals arrived and the match went to an incredibly nerve-racking penalty shoot-out.
Chelsea were 3-2 down after three penalties each and were odds-on to lose, however two consecutive misses from Bayern gave that man Didier Drogba the chance to net the winning spot-kick which he duly did to hand Chelsea their biggest success of all time.
Chelsea Champions League Runners-Up Seasons
2007-2008: Manchester United 1-1 Chelsea (6-5 pens)
From the moment that Roman Abramovich arrived at Stamford Bridge, the big hope was that the club would be able to win the Champions League and be confirmed as the best team in Europe. Having finished second in the Premier League the season before, the 2007-2008 campaign presented the Blues with an opportunity.
The club eased through the group stage, finishing top and not losing a game against any of Schalke 04, Rosenborg or Valencia. A 1-1 draw with Rosenborg was the final game of José Mourinho, however, and Avram Grant was brought in to replace him.
Chelsea beat Olympiacos in the Round of 16, knocked out Fenerbahçe in the quarter-final and got revenge over Liverpool in the semi-final match. Just as with the Premier League, it was Manchester United that stood in Chelsea's way and goals from Cristiano Ronaldo and Frank Lampard meant a penalty shoot-out was required. Sadly misses from John Terry and Nicolas Anelka handed the Red Devils the Champions League.