Chelsea’s Greatest Champions League Knockout Nights

The 2022/23 season at Stamford Bridge has been an unmitigated disaster. The Blues currently lie way down in tenth in the Premier League table, shockingly closer to the relegation zone than league leaders Arsenal.

Champions League qualification also looks impossible, with Graham Potter’s men currently 11 points behind fourth-placed Tottenham Hotspur, and to make matters worse, each team directly ahead of them in the table currently has a game in hand on them. 

Well, qualification for European club football’s premier competition looks like an impossibility through their Premier League performance.

Chelsea’s continental dreams are still alive and well. A 2–1 aggregate victory over Borussia Dortmund in the Champions League round of sixteen at the start of March set them on a collision course with reigning champions Real Madrid in the quarterfinals of the competition, a repeat of the tie which took place at the same stage last season. 

Despite The Blues’ heroics in the Bernabeu, leading 3-0 with less than ten minutes remaining. But a late double salvo from Rodrygo and then Karim Benzema in extra time ensured that it was Los Blancos who progressed. Online soccer odds from betting site Bovada currently makes Manchester City the favorites for the title this season, but while ever Chelsea are alive in the competition, they will feel like they have a chance of winning it. 

Over the last two decades or so, the Stamford Bridge club has had more memorable European nights than most. Admittedly, those nights in Munich and Porto shine brighter than most. But when it comes to two-legged knockout ties, which victories shine brighter than the rest? 

Barcelona 2-2 Chelsea (2-3 on aggregate)

Back in 2012, Chelsea was having a season just as disastrous as the one they’re enduring today. New manager André Villas-Boas was dismissed after barely seven months in charge following a 1-0 defeat away at West Bromwich Albion.

Club legend Roberto Di Matteo was appointed as manager on an interim basis, and no one could have predicted the job he was about to embark upon. 

The Italian’s first job as acting manager was overturning a 3-1 deficit against Napoli in the Champions League round of sixteen. After a chaotic night at The Bridge, Chelsea did exactly that courtesy of an extra-time winner from Branislav Ivanović, giving them a 4-1 victory on the night and 5-4 victory on aggregate.

After that, Benfica were handily dispatched in the quarterfinals following victories both home and away, setting up a mouth-watering semifinal against the holders and favorites Barcelona.

With Barcelona’s greatest manager Pep Guardiola, the squad was at the pinnacle of its powers, led by Lionel Messi and backed by the likes of Xavi and Andrés Iniesta. Chelsea meanwhile had an aging squad looking for one last hurrah, but no one truly expected them to progress against the Catalonians.

In the first leg at Stamford Bridge, The Blues somehow walked away with a 1-0 victory courtesy of Didier Drogba’s first-half strike, but it was in the Nou Camp where the club would have one of their greatest ever nights. 

Di Matteo’s men had a dreadful first half. Sergio Busquets wiped out the one-goal lead in the 35th minute, two minutes later captain John Terry was dismissed for kicking out at Alexis Sánchez, and six minutes on from that Iniesta gave the hosts a 2-0 lead on the night, and enough to progress to the final.

Practically straight from the kick-off however, Frank Lampard fed Brazilian midfielder Ramires, who dinked over Victor Valdes giving the visitors the all-important away goal. 

As the second half got underway, Chelsea suddenly had something to defend, and if they could hold on, they would progress to the Munich showpiece on away goals. Messi struck the crossbar with a 49th-minute penalty, and the stars were beginning to align. 

Wave after wave of Barcelona attacks were thwarted and then in the 92nd minute, Fernando Torres found himself bearing down on goal with no defenders in sight. He duly rounded Valdes before slotting home and sending the travelling fans, bench, and players into raptures.

The Spaniard repaid his £50m transfer fee with one goal, and Chelsea could celebrate reaching their second Champions League final in four years. 

Chelsea 4-4 Liverpool (7-5 aggregate)

Back in 2009, Chelsea met Liverpool in the Champions League for the fifth consecutive season. In the early years, it was the Reds who held the advantage, winning two semifinals against their London rivals. In 2008 however, Chelsea bucked that trend, winning a semifinal of their own. 

In 2009, the pair met once again, this time at the quarterfinal stage, and it was The Blues who shone brightly in the first leg at Anfield. Two second-half goals in five minutes from Ivanović and Drogba gave their side a 3-1 win on enemy territory.

Rafa Bentiez’s side headed south knowing that they needed to score at least three times, without injured captain and talisman Steven Gerrard, in order to have any hope of progressing. 

Within just 28 minutes however, the visitors were two-thirds of the way to their target thanks to an unbelievable free-kick from fullback Fábio Aurélio and a Xabi Alonso penalty.

Liverpool needed just one goal in the second half to complete the turnaround however, it was the hosts who came out firing. Goals from Drogba, Frank Lampard, and a thunderbolt of a freekick from Alex gave them a 3-2 lead and surely safe progression to the semifinals. 

Benitez removed his star striker and would-be-Blue Fernando Torres knowing that the tie was all but lost. But then, two goals in two minutes from Lucas Leiva and Dirk Kuyt suddenly put Liverpool 4-3 up on the night and within one goal of progression.

They would push for the goal that would send them through, but Lampard would net his second on the night in the 89th minute, ending the contest once and for all and setting up another semifinal against Barcelona.