When Chelsea first hosted a Champions League qualifier in August 1999, their situation was rather different.
They were newbies to the competition, having never competed in the European Cup before it was reformatted in 1992, and they had to work their way past Latvian side Skonto Riga to play in the competition proper. But after their 3-0 aggregate win over Skonto, their journey began.
On Wednesday night, Ajax visit Stamford Bridge. It will mark Chelsea’s 200th fixture in the competition proper. And it is a journey that has taken in two Champions League trophy wins, three different sets of owners, countless managers, and one ‘ghost goal’.
To mark the moment, The Athletic has asked its Chelsea writers, people who’ve covered Chelsea games, and Chelsea-adjacent contributors for their standout Chelsea Champions League memories…
Barcelona 2-2 Chelsea — April 24, 2012
Chelsea were down to 10 men, had just fallen 2-0 behind (losing 2-1 on aggregate) a few minutes before the interval, and were facing one of the greatest teams ever seen. Playing at centre-back were right-backs Branislav Ivanovic and Jose Bosingwa.
I remember joking high up in the press box, “All Chelsea have to do now is score and they will go through on away goals.” Seconds later, Ramires chipped Barcelona goalkeeper Victor Valdes to silence most of the Camp Nou.
Chelsea’s rearguard action against Lionel Messi & Co was truly astonishing. Yes, luck was required, but so was grit and determination. Fernando Torres waltzing around Valdes late on simply provided the icing on the cake.
This was not just one of the most extraordinary results in Chelsea’s history, but by any British club.
Simon Johnson, Chelsea correspondent
Chelsea 1-1 Barcelona — May 6, 2009
For a time, it felt like Chelsea were cursed in the Champions League. After semi-final defeats at Monaco in 2004 and Liverpool in 2005 and 2007, and the agony of the Moscow final in 2008, perhaps the most bitter pill of them all was the dramatic and highly controversial semi-final defeat by Barcelona in 2009.
As a frenetic second leg at Stamford Bridge entered stoppage time, I filed a match report lauding Chelsea’s remarkable performance in overcoming a brilliant Barcelona team — Xavi, Iniesta, Messi et al — and referee Tom Henning Ovrebo’s… erm … eccentric refereeing decisions, to reach the final, having held on superbly after Michael Essien’s early goal.
And then, with almost the last kick of the game, Iniesta scored an away goal that turned the tie on its head, sending Barcelona to the final and sending Chelsea’s players — most notably Didier Drogba — into a rage at the Norwegian referee who had rejected a series of penalty appeals.
Drogba confronts Ovrebo after the final whistle (AMA/Corbis via Getty Images)
That sense of pandemonium spread to the press box, where we were left frantically rewriting our match reports with first-edition deadlines looming. It was one of those nights that scrambles the minds of players, fans and reporters alike — and quite clearly referees, too.
Oliver Kay, senior writer
Manchester City 0-1 Chelsea — May 29, 2021
This Champions League final did not follow the script. It was supposed to be a fairytale ending to Sergio Aguero’s Manchester City career and the coronation of the Pep Guardiola juggernaut.
With Chelsea having only four months under the leadership of new manager Thomas Tuchel, this final was supposed to come just too soon. They were not meant to win.
Instead, Kai Havertz netted the winner from Mason Mount’s defence-splitting pass, City’s first European title had to wait, and after all that, Tuchel was sacked less than 18 months later.
Cerys Jones, Chelsea correspondent
Chelsea 4-4 Ajax — November 5, 2019
As close to a “that game had everything” game as you’re ever going to get.
There were eight goals, two further goals disallowed, two red cards, two penalties and more besides. Chelsea were 4-1 down after Hakim Ziyech set the bar of expectation way too high for what supporters could expect from him when he signed less than a year later.
Kurt Zouma went on a marauding run that nearly resulted in the greatest goal in Champions League history. Two Ajax players got sent off in the same phase of play, Reece James became Chelsea’s youngest Champions League goalscorer when he volleyed in the equaliser, and Erik ten Hag’s Ajax was essentially the ghost of Manchester United past and future.
Matt Davies-Adams, host of Straight Outta Cobham
Chelsea 2-0 Real Madrid — May 5, 2021
N’Golo Kante is that rare example of a Chelsea legend who is not underappreciated by fans of rival clubs — the Frenchman’s ability to dominate games while remaining humble endeared him to all.
It felt fitting that Kante had arguably his best Chelsea performance with the eyes of the world on him. He excelled against Real Madrid at Stamford Bridge and was heavily involved in both goals. After Chelsea had missed several chances to extend their lead, it was Kante who typically won the ball back and played in Christian Pulisic, who eventually teed up Mason Mount.
At the time, it also seemed apt that Cobham graduate Mount had given Chelsea their best moment in several years and firmly marked them as ‘back’.
Luke Bosher, news editor
Chelsea 4-1 Napoli — March 14, 2012
The real rewards were claimed in Munich, but it was the dismantling of Napoli in the second leg of a last-16 tie in 2012 when Chelsea began to believe.
Humiliated in Naples, with Andre Villas-Boas sacked a few days after that 3-1 loss, this had been a club in turmoil. Yet Roberto Di Matteo coaxed form from his senior players and, in the bedlam at Stamford Bridge, the old guard proved their pedigree. Didier Drogba and John Terry levelled the tie. Frank Lampard scored from the penalty spot after Napoli’s riposte to send the game into extra time, with Branislav Ivanovic eventually thumping them into the quarter-finals.
Roman Abramovich and the club’s former striker Andriy Shevchenko joined the players in the home dressing-room post-match. “We proved we’re a team tonight,” Terry told reporters after the game, as reported by The Guardian. “That’s what we’re about: that desire, that togetherness and sticking together when it really mattered.”
“Back before the second leg of the Napoli game, I’d said to my wife: ‘If we get through this tie, we’ll win it all’,” Petr Cech later admitted.
“Everything was going wrong, the manager had left, we were nowhere in the league, but all our luck was coming in the Champions League. You could kind of feel something was happening.”
Dominic Fifield, commissioning editor
Chelsea 3-1 Barcelona — April 5, 2000
In 2000, I was in Chelsea’s reserve team and was fortunate to get a seat in the Matthew Harding Lower stand for every fixture.
The first leg of the 2000 quarter-final against Barcelona stands out in what was such an exciting time to be at the club. The growth on and off the pitch was huge and despite me having seen Gianfranco Zola, Marcel Desailly and Didier Deschamps at close quarters, it was still somewhat surreal to see them dismantling a Barcelona team containing Luis Figo, Rivaldo and Patrick Kluivert.
Zola battling with Xavi for the ball at Stamford Bridge (Gerry Penny/AFP via Getty Images)
I remember the first half being a blur of goals and chances at the Shed End. Chelsea went 3-0 up in a flash, and there was a sense around Stamford Bridge that we were witnessing something magical.
A Zola free kick, which put Chelsea ahead, stands out in particular. His technique and willingness to practise was something us young players had marvelled at every morning on the training ground.
Despite threatening a second-half comeback when Figo found the net, Barcelona were well beaten, and a European rivalry was born.
Sam Parkin, Straight Outta Cobham contributor and former Chelsea academy graduate
Liverpool 1-0 Chelsea — May 3, 2005
It isn’t a match that Chelsea fans will want reminding of, but Luis Garcia and the ‘ghost goal’ in the second leg of the 2005 semi-final was an iconic moment in Champions League folklore.
Chelsea, a formidable side under Jose Mourinho, had already won the Premier League when they arrived at Anfield, following a forgettable 0-0 in the first leg. Liverpool, by contrast, were struggling domestically and finished the season in fifth, 37 points behind Chelsea.
In an extraordinary night at a frenzied Anfield, however, Liverpool upset the odds. There was early drama as Rafa Benitez’s side took an early lead through Garcia’s highly contentious goal — that is still furiously debated to this day — before defending for their lives. Garcia put his side ahead when he flicked a shot at goal before the ball was cleared away — and it was very difficult to tell whether the ball crossed the line or not before the goal was awarded by referee Lubos Michel.
As Chelsea hunted for an equaliser that would have sent them to the Istanbul final on away goals, there was still time for one last agonising moment in the closing stages, as Eidur Gudjohnsen flashed a shot inches past the post.
It marked the start of a fierce rivalry, with the two sides also meeting in the semi-final of the competition in 2007 and 2008, where Chelsea finally took their revenge on Benitez’s side, before heartbreak in Moscow.
Tom Burrows, football news reporter
Chelsea 4-2 Barcelona — March 8, 2005
I’ll never forget that night. The Bridge was genuinely electric — you don’t always get to say that — and you could feel the tension before kick off, as we somehow needed to overturn a 2-1 deficit against Barcelona without the suspended Didier Drogba.
Out of nowhere, Chelsea were 3–0 up inside 18 minutes, tearing Barcelona apart in scenes reminiscent of the same fixture in 2000. Somehow the game was completely turned on its head before the first half was done, with Ronaldinho pulling Barca back into the lead on away goals with a penalty and that audacious toe-poke that left Petr Cech frozen.
The mood shifted and everyone inside the Bridge must have thought Barcelona would go on to win the tie but then came captain (leader, legend) John Terry’s towering header (aided slightly by the crafty Ricardo Carvalho) and the roar that followed was unrivalled.
Pure drama, pure passion, and a night for the ages.
Raphael Tuffin, Chelsea season-ticket holder
Bayern Munich 1-1 Chelsea — May 19, 2012
While my mum and dad headed out to Munich for the final, I was stuck at home (against my will) as it was deemed that studying for A-levels was more important than watching Chelsea attempt to lift the Champions League for the first time in their history. In full stroppy teen mode, I decided to host an impromptu viewing party at our house for anyone and everyone who wanted to come.
That run to the final against Napoli, Benfica and Barcelona was the stuff of chaos, delirium and folklore. My nerves hadn’t yet recovered from my night at the Bridge and that Ivanovic winner — or hiding at the top of the staircase during the second leg at Camp Nou because it was physically too distressing to watch. But this game and the stakes that came with it after the heartbreak of Moscow four years earlier took it to a whole new level.
The impossible job. Bayern’s to lose. Suspensions galore. Ryan Bertrand in the starting XI! The Thomas Muller header. The Didier Drogba leveller. The Arjen Robben penalty miss. More Peter Cech heroics in the shootout. Drogba’s moment of destiny. The club’s greatest night reduced to a few bullet points that passed by in a total blur of ecstasy for 17-year-old me.
I really hope my dad isn’t reading this — over 13 years later, he still doesn’t know about the wild scenes that were on show long into the early hours of the morning as I played Suggs’ ‘Blue Day’ on repeat and sobbed tears of joy and utter disbelief.
Lucy Oliva, Audio Producer