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The Chelsea story and the European title that got away

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Apart from the friendly games of the International Champions Cup in the United States, Real Madrid vs. Chelsea has been one of the rarest encounters in European football. The last official game between these two sides took place 23 years ago. Some of the players from the current squads were not even born. After almost two and a half decades later, the backdrop and energy of this tie are now completely different.

Perhaps, the aftermath of the proposed (and then swiftly dissolved) European Super League provides the opportunity to make this tie about things that are not within the scopes of two expert tacticians — Zinedine Zidane and Thomas Tuchel. But, on our agenda, is another trip down memory lane. Real Madrid and Chelsea have faced off in just three official games. Twice in the two-legged final of the UEFA Cup Winner’s Cup in 1971 and once in the UEFA Super Cup of 1998.

The European Title that Got Away

Real Madrid have won everything in European football except one. They have lifted the European Cup and its rendition (The UEFA Champions League), the UEFA Cup (currently known as the Europa League), and the UEFA Super cup — all of which have their presence in the Santiago Bernabeu Trophy room in multiple numbers. However, the UEFA Cup Winner’s Cup is the one that got away. Active from 1961 to 1999, the tournament consisting of Europe’s domestic Cup winners wasn’t officially recognized by UEFA until 1963. It eventually got absorbed into the UEFA Cup.

It is perhaps not entirely surprising that Real Madrid never won this competition if you take their (relatively) poor record in Spain’s premier cup competition, Copa del Rey. Real Madrid won the Copa del Rey eight times in the 39 years when the Cup Winner’s Cup was active. They participated in the competition for only four of those years.

Real Madrid made it all the way to the final of the Cup Winner’s Cup in their very first attempt. In the final, they met Dave Sexton’s Chelsea — The FA Cup winners of 1970. Real Madrid got to the final of CWC 1971 with great second-leg performances in each of the previous four rounds. Ironically, they could not do the same in the final round.

In front of a capacity crowd at the Georgios Karaiskakis Stadium in Greece, Real Madrid walked out on the pitch led by none other than Paco Gento — the only footballer with six European Crowns to his name. The English side were not intimidated though. They opened the scoring in the 56th minute through English forward Peter Osgood. Despite their qualitative superiority, Real Madrid had to wait until the 90th minute to scrap a draw out of the fixture, thanks to the equalizer from Ignacio Zoco. The scoreline remained 1-1 after extra time as well.

Cup Winners’ Cup Final

Photo by A. Jones/Daily Express/Hulton Archive/Getty Images

The replay was played just a couple of days later. Peter Osgood was once again Chelsea’s main man — he doubled Chelsea’s lead in the 39th minute after John Dempsey opened the scoring for the blues in the 33rd minute. Real Madrid kept grinding on for a result and even got a goal 15 minutes from the final whistle. But Sebastián Fleitas’ goal was not enough to avoid defeat and the Londoners claimed their first European silverware. Real Madrid would not face Chelsea again for another 17 years. They would get another shot at the Cup Winners Cup title in 1983, only to lose against another British side: Aberdeen.

The Super League Cup

In 1998, Real Madrid ended their 32 year wait to win the UEFA Champions League for the first time since 1966. The competition had been heavily rebranded by that time and Real Madrid’s six previous triumphs were more than three decades ago. Jupp Heynckes led them to continental glory in 1998 but the poor domestic performances saw him leave the club. Dutch Manager Guus Hiddink was in charge of the team when they took on Chelsea — the reigning Cup Winner’s Cup holders. The ghost of the Cup Winner’s cup just would not leave Real Madrid alone.

Soccer - UEFA Super Cup - Chelsea v Real Madrid - Monaco

Photo by Michael Steele/EMPICS via Getty Images

On paper, it was a bit of a mismatch. Real Madrid fielded a star-studded squad led by Manolo Sanchis. The Madrid starting line-up also had big names such as Raul Gonzalez, Clarence Seedorf, Roberto Carlos, and Fernando Redondo. But Chelsea paid little attention to Madrid’s mighty starting XI. Italian manager Gianluca Vialli’s well-drilled side earned a narrow victory to frustrate Real Madrid in a European final once again. Gus Poyet came off the bench to score the game’s only goal on the 83rd minute. Interestingly, Chelsea’s Champions League-winning manager (in 2012) Roberto Di Matteo played in this game.

The Familiar Faces

Although Real Madrid and Chelsea have only played in a handful of matches, the list of personnel who have shared the colours of both clubs is much longer. Nicolas Anelka, Claude Makelele, Ricardo Carvalho, Michael Essien, Marcos Alonso, Lassana Diarra, Thibaut Courtois, Eden Hazard, Arjen Robben, Christian Panucci, Geremi, Mateo Kovacic, Gonzalo Higuain, Samuel Eto’o and Alvaro Morata — that’s some list! We have UCL winners, LaLiga and Premier League winners, Europa League winners, and World Cup finalists in this lot. Most of these players have at least had a significant impact at either Chelsea or Real Madrid (if not at both).

Real Madrid v SD Huesca - La Liga Santander

Photo by Diego Souto/Quality Sport Images/Getty Images

The Familiar faces do not stop at just players of course. High-profile managers like Rafael Benitez, Guus Hiddink, Jose Mourinho, and Carlo Ancelotti have managed both sides. Mourinho and Ancelotti are especially highly regarded among the Madridistas because of fond memories from the first half of the last decade.


Real Madrid and Chelsea have endured difficult yet contrasting seasons in 2020-21. Despite Chelsea’s costly rebuild, they had to sack Frank Lampard in the middle of the season, and Thomas Tuchel has steadied the ship since then. Zinedine Zidane’s Real Madrid have been decapitated with 50+ injuries this season, still, they are somehow staying afloat in two major competitions in April. All the noise surrounding the Super League will rush out of the window when the first whistle is blown at the stellar facilities of the Alfredo Di Stefano Stadium on Tuesday. Only pure football will matter as two highly professional teams will take center stage. There’s no doubt, a new chapter will be written in their short history when the final whistle is blown at Stamford Bridge in the return leg.

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