We competed in the Inter-Cities Fairs Cup, widely considered the forerunner to the UEFA Cup, in 1958/59, 1965/66 and 1968/69.

The competition was predominantly overseen by FIFA executives until 1971. At that point, UEFA took control and the UEFA Cup was born. It was subsequently rebranded as the UEFA Europa League in 2009.

Chelsea’s involvement in each competition has contained no shortage of drama – and we detail in our reflections on some of the Blues’ most famous European games in the wake of reaching the milestone of 300 such fixtures…

Inter-Cities Fairs Cup

AC Milan 1-1 Chelsea, Chelsea won on coin toss – March 1966

Our last-16 tie against AC Milan in 1966 needed three games and a coin toss to separate the sides.

In the first leg at the San Siro, Chelsea lost 2-1 but were grateful to George Graham for his late goal shortly after Milan, who also missed a penalty, had doubled their lead.

Back at the Bridge in front of almost 60,000 people, Graham and Peter Osgood struck early to give us an aggregate lead, which was wiped out before the break.

With both games ending 2-1 to the home side – and with no penalties – a deciding fixture was required.

Captain Ron Harris lost the coin toss for the venue, so back to Milan we went. Barry Bridges fired us in front and it looked like that would be enough, only for the Italian giants to equalise from a corner in the final minute.

Extra time yielded no more goals, so what next? A coin toss! This time, Harris guessed correctly, raising his arms in the air in jubilation to signal it was Chelsea who would – at last – progress.

Chelsea 2-0 Barcelona – May 1966

We beat TSV Munich 3-2 on aggregate in the quarter-finals to set up a maiden meeting with Barcelona. A new European rivalry was born!

After losing 2-0 in the Nou Camp, Chelsea decided some good old-fashioned direct English football was the way to go back at the Bridge. Ron Harris would later claim we enlisted the local fire brigade to water the pitch and bog down Barca’s passing football.

On, shall we say, a difficult playing surface, the visitors lost their heads and were reduced to 10 men before the interval. Chelsea pressed home their numerical advantage with two late own goals forcing yet another deciding fixture.

Alas, Harris lost the coin toss and on the lush Nou Camp carpet, Chelsea were thumped 5-0, which brought an end to a thrilling European adventure.

UEFA Cup

Hapoel Tel Aviv 2-0 Chelsea – October 2001

Owing to the fragile political situation in the Middle East following the atrocities carried out in the United States on 11 September 2001, six Chelsea players opted out of travelling to Israel for the first leg of our UEFA Cup second-round tie against Hapoel Tel Aviv.

It was still a strong Chelsea line-up, however, with Frank Lampard, John Terry, Gianfranco Zola and Jimmy Floyd Hasselbaink all starting. With four of the six absentees defenders, 17-year-old Joel Kitamirike was handed his Blues debut alongside Terry at centre-half.

In a hostile atmosphere, Mario Melchiot was shown a straight red for an off-the-ball incident early in the second half. Chelsea dug deep, helped by the heroics of Mark Bosnich between the posts, but goals in the 89th and 93rd minute condemned us to defeat.

Despite having the six players back for the return leg in London, we could only draw 1-1, bowing out 3-1 on aggregate.

It was the second of three poor exits from the UEFA Cup in consecutive seasons, with St Gallen knocking us out the year before and Viking Stavanger doing so in the autumn of 2002.

Europa League

Chelsea 3-1 Steaua Bucharest – March 2013

The Blues dropped down into the Europa League in December 2012 after an ignominious defence of our Champions League crown. Our last-16 opponents were Steaua Bucharest, who won the first leg 1-0 in Romania.

Back at the Bridge, Juan Mata levelled things up in front of the Shed. However, Steaua bagged an away goal on the stroke of half-time, meaning we now had to win by two.

On the hour, a John Terry header reignited our hopes of progressing and with 19 minutes remaining, Fernando Torres worked a yard of space and drilled a superb left-footed finish into the far corner.

With Torres later missing a penalty, it would prove the decisive goal as we progressed 3-2 on aggregate.

Benfica 1-2 Chelsea – May 2013

After smoother aggregate wins over Rubin Kazan and Basel in the quarters and semis, Benfica stood between us and the right to be Champions League and Europa League holders simultaneously – if briefly!

The Portuguese side, who had lost six consecutive European finals, were the better team for vast swathes of a tight contest, but it was Torres who struck first at the end of a run that blended speed, skill and strength.

Benfica drew level from the penalty spot - Cesar Azpilicueta punished for handball – but it was Chelsea who had the last laugh.

A deep Mata corner found Branislav Ivanovic, who matched Didier Drogba in Munich 12 months earlier by producing one of the all-time great Chelsea headers.

It looped high into the Amsterdam sky and dropped just under the crossbar, ensuring we became the first English team to have won every UEFA trophy.

Chelsea 1-1 Eintracht Frankfurt (4-3 on pens) – May 2019

Two evenly fought legs against an exciting Eintracht outfit ended 1-1, meaning penalties were required to separate the sides at Stamford Bridge.

Azpilicueta blinked first, as Eintracht opened up a 3-2 lead after three penalties each. Azpi’s Basque team-mate Kepa Arrizabalaga came to his and our rescue.

First, he brilliantly trapped Martin Hinteregger’s fierce effort under his shin having stood his ground, and then guessed right to keep out Goncalo Paciencia’s strike.

Up stepped Eden Hazard, in what would prove his last game at Stamford Bridge as a Chelsea player, to coolly send us to Baku. Arsenal awaited…

Chelsea 4-1 Arsenal – May 2019

A big London derby played 2500 miles away in Azerbaijan made for a surreal setting for a major European final, perhaps explaining an uneventful first half.

The showpiece burst into life following the interval and it was Chelsea who seized control. Olivier Giroud brilliantly steered a header past Petr Cech to put his former club on the back foot, and we rammed home our advantage through a typically sweet Pedro finish.

Hazard – making his final Chelsea appearance – made it 3-0 from the spot, and though Alex Iwobi got one back, our brilliant Belgian rightly had the last word, rounding off a slick counter attack.

Baku was blue, and the Europa League was Chelsea’s once again!