Chapter 9

CHAPTER 9: The quest for the Holy Grail

‘Chelsea's courtship of the European Cup has been heartbreaking and ill-fated. This is their last chance to secure the legacy they crave – and the legacy they deserve. It's hard to recall the last time a side as brilliant and enduring as this Chelsea team failed to win the European Cup.’ 

- The Guardian newspaper ahead of the 2012 Champions League final

When Didier Drogba stood over what would prove the most famous kick in Chelsea history, the club’s past Champions League campaigns weighed heavily on his shoulders. It had been a thrilling if sometimes tortuous journey to that night in Munich in May 2012, but a deep breath and a swing of the Ivorian’s right leg later, and those Champions League demons had been laid to rest. For the first time, Chelsea were the champions of Europe. How we had fought to get there!

Our association with the continent’s elite competition had begun 13 years earlier, prior to Roman Abramovich’s purchase of the club. A Blues side managed by Gianluca Vialli, and containing plenty of stellar names, such as Marcel Desailly, Gustavo Poyet and Gianfranco Zola, felt right at ease mixing it with Europe’s best.

The football was electric and effective, seeing Chelsea through two group stages and producing iconic match-ups against giants of the game, like AC Milan and Lazio. Another, Barcelona, with Figo, Rivaldo et al, awaited in the quarter-finals. An extraordinary first leg, in which the Blues raced into a three-goal lead before half-time, was unlike anything Stamford Bridge had witnessed before. Alas, five of the next six goals in the tie were scored by the Catalans to send them through, but a rivalry had been born.

‘I will never forget the atmosphere, and how happy everyone was in the stadium,’ said two-goal Tore Andre Flo after the first leg. ‘Finally Chelsea could play and beat the better teams in Europe.’

Champions League Years 1999/2000

It was three years before Champions League football returned to the Bridge, but this time the influx of stars that had joined following Abramovich’s arrival meant expectations were higher. After safely navigating the group stage and round of 16, the 2003/04 European campaign’s highlight came at Highbury, where a late Wayne Bridge goal ended a long run without beating Arsenal and secured our place in the last four at the expense of our London rivals. ‘It was when Chelsea began to dominate Arsenal,’ reflected Bridge years later.

Against Monaco in the semi-finals, disaster struck in what was the first of four agonising exits at that stage of the competition. At 2-0 up in the second leg at home, the Blues were heading to the final, but the Principality team fought back, helped by some tactical mistakes and refereeing errors over the two games.

The rivalry with Barcelona was renewed the following campaign. Another epic tie, this time in the round of 16, went our way courtesy of John Terry’s late header at the Bridge, the deciding goal of nine scored over two engrossing legs packed with drama. We then saw off Bayern Munich in the quarters.

JT secures a famous win against Barcelona in 2005

Jose Mourinho’s Blues were marching to a first English league title in 50 years, but it was another Premier League side, Liverpool, who put paid to our European hopes that season. Controversy abounded as Luis Garcia’s second-leg ‘ghost goal’, the only one scored in the tie, was deemed to have crossed the line. Replays proved inconclusive. Either way, we had a new domestic and European foe.

After Barcelona had gained revenge for their defeat a year earlier by eliminating us in 2006, it was heartbreak at the hands of Liverpool in the semi-finals again in 2007, this time in a penalty shoot-out. Chelsea’s Champions League curse went on, and only intensified in the following two campaigns.

It is hard to know which was more painful. In 2008, we finally got the better of Liverpool in the semi-finals, helped by a Drogba brace and Frank Lampard penalty, on an emotional night at the Bridge.

Frank Lampard, in his first game following the passing of his mother, slotted a high-pressure penalty against Liverpool

The Blues were bound for Moscow, but our hopes of lifting the big-eared trophy in the owner’s homeland evaporated in the Russian rain as Manchester United emerged victorious from a penalty shoot-out after a 1-1 draw. Terry had the chance to win it for the club he adored and captained, but lost his footing when he struck his spot-kick.

‘To see Chelsea win the Champions League after what happened in Moscow definitely made those sleepless nights easier,’ our long-time skipper admitted following the Munich triumph.

The suspicion destiny was not on our side in the Champions League only increased 12 months later. This time, a last-minute Andres Iniesta strike for Barcelona – them, again – dumped us out in the semi-finals. Chelsea had dug in at Camp Nou to earn a goalless draw, gone ahead in the second leg through a Michael Essien thunderbolt, and then had a string of penalty appeals turned away as we sought to put the tie to bed prior to Iniesta’s gut-wrenching intervention.

For Petr Cech, Terry, Lampard and Drogba – stalwarts of all but our first two Champions League adventures – it must have started to feel like it was not meant to be.

2010 and 2011 brought relatively limp exits to Inter Milan and Man United respectively, but any notion the team’s European heyday was over was spectacularly quashed in 2011/12 during a Champions League campaign fraught with danger that ended in the greatest glory of them all.

Only victory over Valencia in our final group game secured a safe passage to the last 16, where a 3-1 loss away to Napoli instigated the replacement of Andre Villas-Boas with Roberto Di Matteo, a key member of Chelsea’s very first Champions League squad.

The Blues battled back in the second leg, helped by the old guard of Drogba, Terry and Lampard. The enthralling last-16 tie headed to extra-time. In it, Branislav Ivanovic slammed home what would prove the deciding goal, crowning one of the truly great Stamford Bridge nights. ‘We showed what Chelsea are really made of,’ beamed Terry.

Drogba - The Chelsea Years

After beating Benfica home and away in the quarters, it was Barcelona next. Them again! But perhaps the footballing gods were on our side this time. In the first leg at Stamford Bridge, the visitors missed a host of chances while Drogba took one of the few that came our way.

The second leg was arguably the most extraordinary game in our history. Two goals and a man down to the team many called the greatest of all time, somehow the Blues advanced. On the stroke of half-time, Ramires put us ahead on away goals with a sublime chip, and a heroic rearguard action kept Barca at bay after the interval. Cech made save after save, Lionel Messi hit the bar with a penalty, and then with time almost up, Fernando Torres broke clear to score.

Chelsea had climbed a mountain and some, but there was one more tough peak to scale: Bayern Munich in their own stadium. Missing four players through suspension, 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 improbably equalised 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.

Munich 2012 in slow-motion

‘To fulfil our ambitions as a world club, you have to win the Champions League. You have to win trophies on a regular basis, you have to win the Premier League and Champions League more than once to reach those heights of being truly recognised as a world club.’

- Peter Kenyon – Chelsea chief executive 2004 to 2009


Chelsea’s defence of our 2012 European title and attempt to add a second Champions League trophy to the cabinet did not begin well. We became the first holders to fail to advance beyond the group stage, an outcome which coupled with stuttering league form, cost Di Matteo his job before the 2012/13 season was out.

Going on to win the Europa League instead was a pleasing consolation and the following year, with Jose Mourinho back at the helm, the Blues were back contesting the Champions League later stages.

Didier Drogba made a return to Stamford Bridge with Galatasaray but was defeated and there was pure drama when a 3-1 away deficit against Paris St-Germain in the quarter-finals was overcome, with Demba Ba hitting the winner three minutes from time cueing memorable celebrations.

Manager Mourinho joins in the touchline celebrations for a winner over PSG

Against Diego Simeone’s Atletico Madrid however, with our on-loan goalkeeper Thibaut Courtois between the Spaniards’ posts and future Chelsea players Filipe Luis and Diego Costa in their defence and attack respectively, there was less joy to be had, and a Stamford Bridge defeat knocked the Blues out. We would not make the semi-finals again for another seven years.

The west Londoners may have got the better of PSG that season but the French side soon became a thorn in ours, ending our hopes in the Last-16 stage in 2015, when David Luiz, between his two Chelsea spells, and another who would become a Blues centre-back, Thiago Silva, both headed in at the Shed End.

Thiago Silva beat Chelsea in 2015 but would have to move to Stamford Bridge to win the Champions League

Instead we claimed the domestic crown so back at Europe’s top table under Antonio Conte, there was a reignition of our rivalry with Barcelona when we met the Catalans at the first knockout stage. Finally, and fatally for our hopes, Lionel Messi found the Chelsea net after nine scoreless games against us – once in a draw at the Bridge and then twice in our 3-0 defeat at Camp Nou.

Genuinely challenging for the Champions League again was feeling some way off, and 2018/19 under Maurizio Sarri was another Europa League-winning campaign instead.

In 2019/20 with Frank Lampard freshly at the helm, there was a Champions League group-stage win at Ajax plus the fireworks of a recovery from 4-1 down against the same side to draw at the Bridge, but our knockout-stage exit to the side destined to win the tournament, Bayern Munich, was as convincing as it could be.

Chelsea 4-4 Ajax

Highlights from an outstanding group stage match at Stamford Bridge.

So what were the chances for 2020/21, the mid-pandemic Champions League?

Lampard led a side of young homegrowns mixed with big summer purchases, plus a few important old hands, through the group stage convincingly. A 4-0 win against Sevilla with all the goals by Olivier Giroud stood out especially.

By the knockout rounds Thomas Tuchel, a losing finalist with PSG the previous season, was the coach in charge and momentum, founded on a strong defence, was beginning to build.

Atletico Madrid, for so long formidable opponents for anyone in this competition, were beaten in both legs. Giroud scored again with an outstanding overhead kick in the first leg, and Hakim Ziyech and Emerson netted breakaway goals at the Bridge in the return match, the second one greeted gleefully by non-playing team-mates in the stands, including injured Thiago Silva, who was another defeated finalist the year before.

Thiago Silva, Mason Mount & Jorginho celebrate Emerson's goal v Atletico Madrid

The Blues trio certainly made up for there being no fans inside Stamford Bridge with their wild celebrations of Emerson's match-sealing goal!

As Chelsea were kept in the other half of the draw from the Premier League’s strongest side, Manchester City, and the previous winners and runners-up, Bayern and PSG, hopes rose further, but still there were Porto and Real Madrid ties to be negotiated.

Both Porto games were played in the same stadium in Spain and Mason Mount and Ben Chilwell goals in the first meeting were enough to go through.

With Real Madrid taking the opportunity during Covid lockdown to redevelop their stadium, Chelsea were denied a first game in the Bernabeu, but we impressed at their training ground instead with Christian Pulisic outshining the player whose Chelsea shirt number he had taken, Eden Hazard, in a 1-1 draw.

A thoroughly deserved semi-final win was duly completed at the Bridge with German attackers Kai Havertz and Timo Werner responsible for the first goal in a 2-0 win, and Mount at last converting what had been a host of chances against the greatest side in the competition’s history to complete the win.

Mighty Madrid are defeated as Mount arrives

So it was to the banks of the River Douro in Portugal for our third Champions League final, and second against another English side.

Tuchel’s team had beaten Pep Guardiola’s Man City twice in domestic competition in the preceding weeks, and as in those games, the Premier League champions were prevented from finding their top gears by a cleverly set-up and high-performing Chelsea side.

When Havertz took an excellent Mount pass beyond the keeper and slotted it into the net in the closing minutes of the first half, the lead was no more than Chelsea deserved. Outstanding defending all across the pitch, with 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 victory, raised the trophy in true style, and no one could say victory was not warranted.

Champions League celebrations

Chelsea celebrate with the Champions League trophy!

It had taken longer than the original ambition to win Europe’s biggest competition on more than one occasion, but Chelsea’s status as a world club was now assured.