If APOEL Nicosia are to make it through to the UEFA Champions League semi-finals they will have to pull off arguably the biggest upset in the tournament’s long history by overturning a 3-0 deficit against Real Madrid. While the chances are slim, FIFA.com looks back across a number of results that could inspire the Cypriots at the Santiago Bernabeu. It wouldn’t be the first time the Spaniards have slipped up.

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 Valeri Chmarov, who gave the Muscovites a 3-1 win and a ticket to the semis.

Second-round defeats to Swiss side Grasshoppers and Standard Liege are both notable, but Real’s biggest-ever upset came in 1962 – during their noted European supremacy – at the hands of another Belgian side, Anderlecht.

Fielding the likes of Alfredo di Stefano and Ferenc Puskas, all expected Real in the second round, but a 3-3 draw saw the dominant force in world football booed off the pitch by the Bernabeu fans. The Spaniards were sufficiently blunter in the second leg and with a play-off looking on the cards Jozef Jurion struck to put the five-time champions out, a feat that has seen him known as ‘Mr Europe’ ever since.

The final has seen its surprises too. While giant-killings at the ultimate stage are exceptionally rare, the likes of Hamburg dominating tournament favourites Juventus – who boasted six Italian FIFA World Cup™ winners, Michel Platini and Zbigniew Boniek – in 1983 was one. Another came when Celtic’s ‘Lisbon Lions’ stunned Angelo Moratti’s expensively assembled Inter Milan side in 1967. The biggest, though, was undoubtedly when Steaua Bucharest beat Barcelona in 1986.

Steaua surprise
Barça were yet to win a European Cup, but the Catalans still dwarfed their Romanian opponents, who had largely failed to impress en route to the final. A resolute defensive display in Seville saw the underdogs frustrate Terry Venables' side for two hours, taking the game to penalties. Helmut Duckadam then stole the show with a monumental performance – saving all four spot-kicks he faced – which saw the trophy go to eastern Europe for the first time.

Barcelona have had trouble with eastern European sides since then too. A 2-1 win saw Rubin Kazan silence the Camp Nou in 2009, but Dynamo Kiev pulled off an even great shock 12 years earlier by putting seven past the Catalans without reply across two games, with Andriy Shevchenko scoring three in Spain. The results were terminal, seeing the likes of Luis Figo and Rivaldo finish bottom of their group.

However, in the competition’s first year as the Champions League in 1992, they stumbled again, as CSKA Moscow produced one of the cup’s biggest upsets by knocking the then holders out in the second round. Finishing 1-1 in Moscow, it was expected Johan Cruyff’s side would cruise in the Camp Nou. At 2-0 up and nearing the interval it looked a formality, until 15 minutes of play stunned the Catalans.

I have been a manager for eight years and a player for 25 years and this is out-and-out the worst football night I have ever had. Disappointment would be way down my list of adjectives.

Gordon Strachan on Celtic's 2005 loss to Artmedia

A goal from Yevgeni Bushmanov just before half-time provided hope, and then two goals before the hour – capped off by Dmitri Karsakov’s cheeky flick – left the Camp Nou hung in a stony silence. Hristo Stoichkov, Michael Laudrup and Pep Guardiola left the field with their heads hung low in what remains the last time the holders were eliminated before Christmas.

It was a failure matched by Liverpool, who fell at the first hurdle in 1979 after having defended their title earlier that year. A 2-1 win over Dinamo Tbilisi left Kenny Dalglish and Co in a precarious position for their trip to Georgia, but it wasn’t to be a close-run thing. The Reds were thumped 3-0, with a sumptuous second following a dazzling 50-yard run by Georgi Chilaia to set up Ramaz Shengelia’s chipped finish.

End of an era
Ajax arguably suffered even greater ignominy, as they were eliminated in their first tie of 1973 by CSKA Sofia after having won three consecutive titles. Cruyff may have left for Barcelona, but they still had the likes of Johnny Rep, Ruud Krol and Johann Neeskens in their ranks.

They had beaten the Bulgarians 6-1 the season before, but an unconvincing 1-0 win in Amsterdam set up a nervy trip away. CSKA took the game to extra time and, four minutes from a penalty shoot-out, Stefan Mihailov struck to effectively end the club’s period of Total Football.

Inter Milan have suffered a few first-tie exits themselves. Swedish sides have caused the most trouble, with Malmo beating them 1-0 in the preliminaries of 1989, and then Helsingborg repeating the feat in the third qualifying round for 2000/01.

A fine left-footed volley from Mikael Hansson left Inter with a 1-0 scoreline to overturn in the San Siro, but they were still expected to beat Helsingborg comfortably. They struggled until a last-minute penalty looked to have given them a lifeline. However, Sven Andersson turned Alvaro Recoba’s effort round the post to see the Swede crowned ‘San Siro Sven’ by their fans.

Another Italian side was on the end of one of the European Cup’s greatest upsets in just the tournament's fourth instalment. John Charles and Gianpiero Boniperti’s Juventus had cantered to the 1958 Serie A title, but came unstuck in spectacular fashion against Wiener Sport-Club.

A routine 3-1 win in Turin saw Juve travel to Austria expecting easy passage, but they were stunned 7-0, with Josef Hamerl getting four, and recorded a monumental scalp. “Their passes went into the void, players stumbled across their own feet, combinations didn’t work out,” said WSC’s Walter Horak. “They were committed, but once the goals poured in, they lost their will.”

Artmedia avalanche
Celtic may have handed out an upset back in the 1960s, but they were well and truly on the end of one against Artmedia Bratislava in 2005. The Slovakian outfit had won their first national title and hosted the Scottish giants in the second qualifying round having scraped past Kairat Almaty of Kazakhstan after extra time.

The Old Firm side were promptly spanked 5-0 by the minnows in Slovakia. After the game manager Gordon Strachan was frank: “I have been a manager for eight years and a player for 25 years and this is out-and-out the worst football night I have ever had. Disappointment would be way down my list of adjectives.”

Led by Vladimir Weiss – who would later take the Slovakian national team to the last 16 of the 2010 FIFA World Cup – Artmedia won the tie 5-4 and became Slovakia’s second-ever side to reach the group stage. They are also one of only two teams ever to do so by negotiating the entire qualifying round, the other being Liverpool that same year.

In the mid-90s Arrigo Sacchi’s AC Milan were a dominant force. While they may have been beginning to wane, they were still Italian champions and had been to four of the last six finals when Rosenborg knocked out the giants in 1996. Needing just a draw at the San Siro to qualify from their group – and having won 4-1 in Norway – few expected a surprise. Harlad Brattbak defied the odds, though, claiming a goal and an assist against a nervy home side to win 2-1 and reach the quarter-finals.