Narrowing down the multitude of iconic games we have played since first participating in the Champions League in 1999 has been a very enjoyable – although very challenging – task!

And this list is just our selection. If your favourite match hasn’t made the cut, know that on another day it could easily have done so.

We simply had to draw the line somewhere…

Chelsea 3-1 Barcelona – April 2000

Our first Champions League campaign had already been a hell of a ride before Barcelona came to town. We had drawn twice with AC Milan in a pair of heavyweight clashes, won 5-0 at Galatasaray, and held Lazio to a draw at the Stadio Olimpico.

Barcelona's visit for our first knockout tie, the quarter-finals, was something else. The La Liga giants possessed Luis Figo and Rivaldo, two of the world’s best, and were the favourites after avoiding defeat in the two group phases.

But Gianluca Vialli’s Blues showcased their ability to rise to the biggest occasion, racing into a three-goal lead in the space of eight first-half minutes.

Gianfranco Zola whipped in a trademark free-kick (pictured top), which was swiftly followed by two clever Tore Andre Flo finishes. The Bridge was rocking.

Figo got one back in the second half, and the Blues withstood the Barca onslaught to record a historic 3-1 victory. It remains one of our greatest nights, with no gloss taken off it despite losing the second leg in Spain.

Arsenal 1-2 Chelsea – April 2004

Few gave the Blues hope of winning at Highbury and progressing beyond Arsenal in the second leg of our all-London quarter-final tie in 2003/04.

The Gunners were in the midst of an unbeaten league campaign and hadn’t lost to the Blues in five-and-a-half years. In fact, our only two wins against Arsene Wenger’s side in the previous 27 meetings had come in the League Cup.

A 1-1 draw at the Bridge meant we had to score, so when Juan Antonio Reyes fired the hosts ahead on the stroke of half-time, things didn't change a great deal.

Early in the second period, Frank Lampard showcased his predatory instinct to draw us level on the night and on aggregate. Another away goal would put Claudio Ranieri’s Blues in a commanding position.

The Blues began to take control of the game as Arsenal started to fear an unexpected exit and, with five minutes remaining, Eidur Gudjohnsen was denied by a brilliant Ashley Cole goalline clearance – how we would come to enjoy those!

But our pressure paid off soon after as Wayne Bridge exchanged passes with Gudjohnsen and guided a shot past Jens Lehmann to send Chelsea fans delirious. Those years of frustrating meetings with Arsenal were washed away in one moment.

Chelsea 4-2 Barcelona – March 2005

There is an argument to be made that this is the greatest match in our history. It was a night of extraordinary drama at Stamford Bridge.

Trailing 2-1 from the first leg, we raced into a 3-0 lead in not dissimilar fashion to five years prior. Gudjohnsen, Lampard and Damien Duff found the net inside 19 minutes in front of a disbelieving Shed End.

The great Ronaldinho netted a penalty in response and then scored possibly the best goal we have ever conceded, an outside-of-the-box toe-poke that left mouths agape and some home fans applauding.

With that impudent and improbable strike, Barcelona were heading through on away goals. But with a quarter of an hour remaining, John Terry headed home at a corner – with a bit of help from Ricardo Carvalho blocking Victor Valdes – and a quarter-final berth was ours.

Chelsea 3-2 Liverpool AET – April 2008

Liverpool broke our hearts in the semi-finals of 2005 and 2007, but we exacted revenge with a pulsating second-leg victory at the same stage in 2008.

It had finished 1-1 at Anfield a week prior; John Arne Riise’s injury-time own goal – immortalised in Salomon Kalou’s song – giving the Blues a slight advantage.

It would finish 1-1 after 90 minutes at the Bridge, too, with Didier Drogba and Fernando Torres exchanging goals. To extra-time we went.

Lampard kept his composure to score an emotionally-charged penalty following the recent death of his mother and Drogba soon added a third. Ryan Babel’s 117th-minute goal would prove no more than a consolation. At last, we were through to a Champions League final.

Liverpool 1-3 Chelsea – April 2009

Surprise, surprise, the names of Liverpool and Chelsea were drawn together again in the latter stages of the competition, this time the quarters. It was the night a Chelsea legend was born.

Branislav Ivanovic was playing just his 17th game for the Blues and was far from familiar to the wider footballing community. How that would change!

With Chelsea 1-0 down to yet another Torres goal, Ivanovic scored thumping headers either side of half-time, with our lead extended on the break by Drogba.

Anfield was stunned, Ivanovic was the unlikely hero, and an epic 4-4 draw in the return leg ensured the Blues had once again got the better of our Merseyside rivals in Europe.

Chelsea 4-1 Napoli – March 2012

Chelsea legend Roberto Di Matteo’s second game in temporary charge lit the fuse for our run to glory in 2012.

We had lost 3-1 in Italy against a talented Napoli side, but in front of a raucous Stamford Bridge crowd, goals from Drogba and John Terry meant it was advantage Chelsea with 40 minutes remaining of this last-16 tie.

Gokhan Inler half-volleyed Napoli ahead on aggregate, only for a Lampard penalty to take a see-saw contest to extra-time.

There, Ivanovic showcased his happy knack of being in the right place at the right time, blasting us 4-1 up and into the quarter-finals. How Di Matteo and his players danced with joy!

Barcelona 2-2 Chelsea – April 2012

A quite extraordinary game of football, this. Where to start?! Sergio Busquets levelled the tie on aggregate and two minutes later, Terry was sent off in an off-the-ball incident.

With his centre-back partner Gary Cahill having already hobbled off, the Blues had Jose Bosingwa and Ivanovic in central defence, and Ramires at right-back coming up against arguably the greatest club side of all time.

So when Andres Iniesta soon made it 2-0 to the hosts, surely there was no way back?

Unexpectedly – and quite brilliantly – Ramires chipped us ahead on away goals on the stroke of half-time after sprinting on to a pinpoint Lampard pass.

The phrase one-way traffic was invented for what followed in the second period: 10-man Chelsea barely made it out of our own half. Lionel Messi thumped a penalty against the crossbar as Barcelona launched wave after wave of attacks; we needed Petr Cech at his best and lady luck to fall in our favour on a couple of occasions.

Then, as we entered the 90th minute and with the finishing line in sight, a moment Chelsea fans will never forget.

Ashley Cole’s clearance freed Torres, now a Chelsea player, with half the Nou Camp pitch to run into and no Barcelona player in sight. The Spaniard rounded Valdes to score and all that tension was released with the next kick of a ball. Somehow, Chelsea were heading to Munich!

Chelsea 1-1 Bayern (4-3 on pens) – May 2012

The drama was not over...far from it! In our second Champions League final, playing Bayern in their own backyard with four players suspended, the Blues again deployed organised, resolute defensive tactics.

The ‘home’ side’s Thomas Muller headed Bayern in front in the closing stages, but Chelsea would not be beaten as Drogba’s bullet header brought us level with a couple of minutes remaining.

Cech saved a penalty from his former team-mate Arjen Robben in extra-time, and two more in the shoot-out.

That left Drogba with the chance to bring Chelsea’s rollercoaster quest for the Holy Grail to a conclusion. It was one he did not pass up.

After so many heartaches – Monaco, that ghost goal, penalty losses to Liverpool, Moscow, Iniesta’s last-gasp stunner – Chelsea were finally the champions of Europe.

Manchester City 0-1 Chelsea – May 2021

Chelsea expertly and altogether more calmly navigated the knockout stages in 2021, mid-pandemic. The highlight was an impressive 3-1 semi-final aggregate win against Real Madrid, the competition’s most decorated club.

Standing between us and another Champions League crown were Manchester City, comfortably England’s best that season but beaten twice by the Blues in domestic competition leading up to the final.

As in those games, Thomas Tuchel’s cleverly set-up and high-performing Chelsea side prevented City from finding top gear in Porto.

A lead given to us in the closing minutes of the first half by Kai Havertz was no more than we deserved. Outstanding defending all across the pitch, with the indefatigable N’Golo Kante in midfield named man of the match, kept it intact.

Cesar Azpilicueta, who had joined the summer after our first Champions League triumph, raised the trophy in true style.

Nobody could say victory was not warranted, and with restrictions easing to allow some Chelsea fans to attend, the party went long into the night.