Biggest Upsets in European Cup/Champions League History

Footballing tournaments such as the World Cup, the European Championships and the UEFA Champions League, formely the European Cup always leave open a window of opportunity for improbable results to become possible. In the case of the Champions League/European Cup, it’s a much more unpredictable tournament than you might think, despite the best teams in the world squaring off against some of Europe’s minnows. However, results in this tournament have never been particularly cut and dry. In this list, I will be looking at some of the biggest upsets seen in the tournament’s history, both in its current and previous format

Some of these matches involved teams overcoming almost insurmountable deficits to progress to the next round, while other matches were Champions League finals that involved teams having to go to the penalty shootout to decide the winner – at least once after a thrilling lead was cancelled out by the time the 90 minutes were up.


Barcelona 0-0 Steaua Bucharest (Steaua Bucharest won 2-0 on penalties, European Cup Final, 1986)

Steaua became the first Eastern European side to win the European Cup in 1986, as they produced a remarkable victory over the Spanish La Liga champions Barcelona, who enjoyed tremendous support with the final being played in Seville. It is very unlikely that you will see a Romanian side win the biggest prize in European club football again.
Steaua Bucharest defeated the odds and a much stronger Barcelona side managed by Terry Venables. The game itself was dull, with the favourites doing all the attacking and the underdogs playing for penalties from the start.
The Romanian side benefited hugely from the heroics of goalkeeper Helmuth Duckadam, who followed keeping a clean sheet in the match, by going on to save all four of Barcelona's penalties to help win the cup, and a result he was known as the ‘Hero of Seville.’
Steaua, who had not previously triumphed in any European competition, went on to claim the Super Cup later that year, while they finished as runners-up to AC Milan in the European Cup in 1989.


Chelsea 4-1 Napoli (2nd leg, Champions League, round of 16, 2011/2012)

Under the brief management of Roberto Di Matteo, Chelsea’s hopes in the 2011-12 Champions League looked all but dashed against Napoli of the Serie A, after losing 3-1 to the Italian outfit in the first leg of the Round of 16. However, the second leg at Stamford Bridge would see a dramatically different outcome in favour of the Blues: Didier Drogba and John Terry opened the scoring at 2-0, though Chelsea were again in hot water when Gökhan Inler cut the deficit in half for Napoli in the 55th minute. Luckily for Chelsea, a Frank Lampard penalty and an extra time goal by Branislav Ivanović were enough to complete a dramatic comeback leading up to Chelsea’s eventual Champions League victory that season.


Barcelona 0-4 AC Milan (Champions League Final, 1994)

A final remembered not just for the surprising scoreline, but for the fantastic quality of an attacking master class by the Milanese. It was only two years earlier that Johan Cruyff’s Barcelona had won the European Cup at Wembley and defenses in La Liga and Europe continued to be terrorized by a lineup boasting players including Romario, Ronald Koeman, Michael Laudrup and Hristo Stoichkov. Milan went into the game in Athens minus suspended defenders Franco Baresi and Bruno Costacurta, as well as long term injury Michael Van Basten, a two-time World Player of the Year.
The Catalans were heavily fancied but Fabio Capello's AC Milan had other plans: two goals from Daniele Massaro in the the first half put the Rossoneri 2-0 up, before Dejan Savićević and Marcel Desailly added two more before the hour mark. It would be enough to see Milan take home the Champions League trophy in style, by what is still the biggest margin of a defeat in a Champions League final. That same season, Milan went on to win their third consecutive Scudetto.


FC Basel 2-1 Manchester United (Champions League, group stage, 2011/2012)

FC Basel made it into the Champions League round of 16 for only the second time in their history with a stunning 2-1 home win over Manchester United.
It was a result which saw three-time European champions United crash out of the competition at the group stage for only the third time in 17 years.
Needing only a point to knock out Basel and secure their passage into the last 16 from Group C, the Red Devils were the overwhelming favourites and going into the game seemed much more likely to win.
But it all went downhill after Marco Streller put the hosts ahead on nine minutes. United captain Nemanja Vidic went off injured soon after, and the visitors were ultimately made to pay for their wasted chances going forward and vulnerability on the counter-attack, with Alexander Frei putting Basel 2-0 up and out of reach in the 84th minute. Phil Jones put United back in it at 2-1, but it was too little too late for the world football superpower, with Basel securing the most unfancied home win in their history.


Dinamo Tbilisi 3-0 Liverpool (Dinamo Tbilisi won 4-2 on agg: European Cup, first round, 1979/1980)

Teams from behind the Iron Curtain were always shrouded in mystery – in previews they were habitually referred to as "the crack Soviet outfit" or "the ruthless Red Army" but no one knew for sure how good they would turn out to be. Would Tbilisi be as nifty as Ferencvaros and Red Star Belgrade had proved when upsetting Liverpool earlier in the decade, albeit before Bob Paisley had elevated the club to a higher level with two European Cup triumphs?
No. They would turn out to be better than anything the English champions had ever encountered. Already in the first leg at Anfield, where the home side had prevailed 2-1, Dinamo had shown flashes of a technical and tactical sophistication that perplexed the hosts. In Tibilisi came the full onslaught.
Liverpool barely slept the night before the match – some 200 Dinamo fans having staged a torchlight parade around their hotel at 4am – but mostly it was Dinamo's rapid passing and jagged running that made them so sluggish. Dinamo made it 1-0 on the night after a moment that should feature permanently in the Match of the Day intro footage: David Kipiani dazzled past Alan Hansen with a piece of trickery that left the acclaimed denouncer of diabolical defending floundering like a drunk in the dark. Ray Clemence diverted the ensuing cross, but only as far as Vladimir Gutsaev, who slammed it into the net. The Georgians' second arrived in the 75th minute when Georgiy Chilaya collected the ball in his own half, slalomed past three opponents and slipped in Ramaz Shengelia, who casually lifted the ball over Clemence to make it 2-0.
Three minutes later came the third after Phil Thompson conceded a penalty and Alexandre Chivadze converted with ease.
Hansen has since said this was the best Liverpool team he ever played in. Kevin Keegan's Hamburg would avenge them in the next round, knocking out Dinamo.


Barcelona 1 Rubin Kazan 2 (Champions League, group stage, 2009/2010)

The Russians beat defending champions FC Barcelona 2-1 in the Group F game, despite Barca virtually fielding their strongest line-up—with Lionel Messi, Zlatan Ibrahimovic, Andres Iniesta, Yaya Toure, Xavi, Gerard Pique, Dani Alves, Eric Abidal and Victor Valdes all starting for Barca.
Aleksandr Ryazantsev gave the visitors a shock lead after just two minutes, with a stunning 30-yard strike.
Ibrahimovic equalised for Barca just after half-time, and despite the hosts brutally asserting their dominance over their inferior counterparts, it was Rubin Kazan who re-took the lead, with Gokdeniz Karadeniz coolly slotting past Valdes to stun the Camp Nou crowd, and the watching world. Before the game, Rubin Kazan were 22/1 to win.


CSKA Sofia 2-0 Ajax (CSKA Sofia won 2-1 on agg: European Cup, second round, 1973/1974)

Ajax had been shocked before – not least in 1960 when they were beaten 4-3 by the Norwegian amateurs Fredrikstad – but those defeats came before they had evolved into the European powerhouse of the early 1970s. This came when they were close to the height of their powers. In 1971, '72 and '73 they had won a hat-trick of European Cups under Rinus Michels and then Istvan Kovacs. Johan Cruyff had departed for Barcelona in the summer of 1973, but this was still the team of Johan Neeskens, Arie Haan, Johnny Rep and Piet Keizer. They had not been beaten in Europe since the defeat to Arsenal in the semi-final of the Fairs Cup in 1969-70. They had won six of the previous eight Dutch Eredivise titles.
CSKA by comparison, despite their domestic success (four back-to-back titles from 1969), had never made an impact on the European scene. They'd reached the European Cup semis in 1967 but in the previous year's European Cup they had been destroyed 6-1 over two legs by the same Ajax side. They'd reached the second round in bizarre circumstances after their second leg with Panathinaikos was replayed after the game had gone to penalties. A Jan Mulder goal gave Ajax a 1-0 victory in the first leg, but that was nullified in Sofia when Dimitar Marashliev scored in the 68th minute.
Extra-time was needed. In the 116th minute, Stefan Mikhailov struck to give the Bulgarians a famous victory and effectively end Ajax's golden era. It was to be 14 years before the once-dominant club won another European title.


Chelsea 2-2 Barcelona (Champions League, quarter-final, 2011/2012)

Following the comeback against Napoli, Chelsea faced much more fearsome opponents in Barcelona in the quarterfinals. A 1-0 victory at Stamford Bridge courtesy of a Didier Drogba goal was hardly a reassuring lead, and the odds against them keeping their lead at the Nou Camp were small. Furthermore, John Terry would get sent off in the 37th minute, reducing Chelsea to 10 men for the rest of the match. However, Chelsea again caused an upset after Sergio Busquets and Andres Iniesta put the Blaugrana up 2-0, the game seemed a forgone conclusion, with even some of the Chelsea players clearly thinking the match was beyond their reach.
Even when Ramires levelled just before halftime, still the game seemed out of Chelsea's hands. But after a missed Lionel Messi penalty and a Fernando Torres equaliser, it was the Londoners who had shocked the world and made it through to only their second ever Champions League final.


Real Madrid 1-3 Spartak Moscow (S.Moscow won 3-1 on agg: European Cup, quarter-final, 1990/91)

Spartak went into this match on the back of early round victories over Sparta Prague and Napoli.
Having ground out a 0-0 draw at Spartak Moscow, Real would have been confident of putting the Russians to the sword back in Madrid during the 1990/91 quarter-finals. That confidence would have only been bolstered once Emilio Butragueno had struck on nine minutes, considering it was Los Blancos’ 22nd goal of the tournament.
That lead didn’t last long, though, and Real were behind before half-time. The likes of Hugo Sanchez had no reply and the final word went to Dmitri Radchenko and Valeri Shmarov, who gave the Muscovites a 3-1 win and a ticket to the semis. Unfortunately Spartak lost the semi-final to Marseille, a Club who were very much in their most succesful era of all-time, and included in their team the likes of Basile Boli, Abedi Pelé, Jean-Pierre Papin and Chris Waddle.


Bayern Munich 1 Manchester United 2 (Champions League Final, 1998/1999)

As the Champions League trophy stood decked out with Bayern Munich’s ribbons and with 90 minutes on the clock, the two teams played out the conclusion to a hitherto unremarkable final.
Bayern Munich looked to have done enough to deserve to win the trophy following a first-half Mario Basler free kick which had put them in the lead. With three minutes of injury time remaining on the clock, Manchester United managed to snatch victory from the jaws of defeat with two quick fire goals from Teddy Sheringham and "super sub" Ole Gunnar Solksjaer. The Germans were left stunned in what was to be Peter Schmeichel’s last game between the sticks for United.


AC Milan 3-3 Liverpool (Liverpool won 3-2 on penalties, Champions League Final, 2005)

The "Miracle of Istanbul", the 2005 UEFA Champions League Final between AC Milan and Liverpool will forever be remembered as one of the greatest finals in world football history.
Almost every football fan knows the tale of this final—played at the Ataturk Olympic Stadium in Istanbul—in which Milan went 3-0 up at halftime.
At that point, it was shaping up to be one of the most one-sided finals ever, with AC Milan playing some of the most beautiful football seen in a Champions League final.
The result seemed a forgone conclusion just 60 seconds into the encounter, when captain Paolo Maldini volleyed home Andrea Pirlo's free-kick cross to put Milan 1-0 up, before a Hernan Crespo brace before halftime seemingly sealed Liverpool's fate.
Even on 54 minutes when Steven Gerrard gave Liverpool a lifeline and scored to make it 3-1, the final result never seemed in doubt. But what happened next changed football history forever.
Given space on the edge of the Milan penalty area, Vladimir Smicer hit a powerful yet hopeful shot which somehow found it's way past the Italian's packed defence and in to the bottom corner past Milan goalkeeper Dida.
With the score at 3-2 and Liverpool now attacking fast and full of hope, nerves got the Milan defence as they conceded a penalty as Gennaro Gattuso fouled Gerrard in the box.
Xabi Alonso stepped up and scored the penalty, putting Liverpool back in the game at 3-3, and, far more remarkably, making AC Milan's certain Champions League win completely crumble in the space of just six minutes.
A penalty shoot-out followed and the comeback was complete with Šmicer, Dietmar Hamann and Djibril Cissé converting for the Reds to win them a fifth European title in one of the greatest comebacks ever seen in the sport.