Wiener Sports Club 7 Juventus 0 (agg: 8-3)
(Qualifying round second leg 1 October 1958)

When you see a result as nonsensical as this, it's instinctive to presume a catch. Maybe the milieu was different and Juventus were rubbish in those days? But then you remember that this was the Champions Cup, and that suckers are no more likely to win Serie A than patsies are to win a femme fatale, and then you see a teamsheet that includes John Charles, Giampiero Boniperti and Omar Sivori. Maybe WSC, who are now in the Austrian Regional League East, were one of Europe's top sides at the time? A 7-1 defeat to Real Madrid in the quarter-finals would suggest otherwise. Perhaps, this being before substitutions were permitted, they had a flurry of injuries and were reduced to eight men? Nope. This is a scoreline without an asterisk against it, and as such must surely be the most startling result in the game's history. Like Christopher Nolan films and the opposite sex, it will never be fully understood.

The first leg in Turin was fairly routine, with Sivori's hat-trick giving Juventus a 3-1 victory, and few expected problems when they went to Austria. The first 25 minutes of the match passed peacefully, too, but then the orgy of net-bothering began. Karl Skerlan opened the scoring, Josef Hamerl smacked four, and Erich Hof scored two late goals to apply whatever goes on top of the cherry on the icing on the cake. It was an astonishing rout that put the 'Tor!' in 'torture'. Yet there could have been more goals. WSC also hit the woodwork twice and missed a number of chances.

Juventus had no answer.

"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. Some acted ugly. Sivori and [Rino] Ferrario were looking for trouble."

WSC were no shrinking violets. They scored seven goals and kicked seven bells out of Juventus. Charles — one of the few to abstain from the rampant physicality — almost lost his left leg as a result. "This game was the most frightening episode of my career," he said in his autobiography. "I was kicked so much by the Austrian defenders that I heard the doctors in the Molinette Hospital in Turin discussing whether or not they might need to amputate my legs. For a while it was genuinely touch and go whether I would lose my left one. I became feverish and had to spend a month in hospital, receiving injections every few hours because of the pain I was suffering."

His legs would eventually heal but, for the Old Lady of Juventus, the scars of their heaviest European defeat, will never go away.

Anderlecht 1 Real Madrid 0 (agg: 4-3)
(First round second leg 26 September 1962)

In a sense it's a shock every time Real Madrid are eliminated from the European Cup, such is their indelible association with the tournament. But they have suffered many surprises in the conventional sense. In the European Cup alone they have been knocked out by Rapid Vienna, Standard Liège, Brugge, Grasshoppers, Spartak Moscow, Monaco, Lyon — and, most stunningly of all, Anderlecht in 1962.

Nearly 50 years on, the result still makes no sense. Madrid had won the first five European Cups from 1956 to 1960. In the two seasons before this match, they had lost close contests to two excellent sides, Barcelona and Benfica. They might have been a touch past their best — Ferenc Puskás and Alfredo Di Stéfano had a combined age of 71 — but they would still be good enough to come again and reach the final the following season. For a team as good as Madrid's, losing to anything less than the best was a felony.

Anderlecht were significantly less than the best. They had never won a European Cup game. They had a record so dismal that even a mother might ostracise it: played six, lost six, conceded 29. They would eventually lose 6-2 on aggregate to Dundee in the quarter-finals. On the face of it they had two chances as they went to Madrid, and slim had forgotten to pack his passport.

Yet Anderlecht somehow managed to draw the first leg in the Bernabéu 3-3, after trailing 2-0 and then 3-2, setting up a compelling second leg three weeks later. There was no away-goals rule in those days, so the match would have to be won. The consequence was a cautious, tactical contest that was not decided until the 85th minute when Jef Jurion, sporting his trademark rubber-strapped glasses, lashed the loose ball into the bottom corner from 20 yards after his first shot had been blocked. "It was the first time in my life," he later said, "that I put the ball exactly where I wanted."

The most famous words on the subject came from Rik De Saedeleer, whose commentary has been immortalised. As the ball came to Jurion, he said simply: "Jef, do something. Jef! Goal! Goal!" Not, then, the catchiest title for a comedy show, as England's most famous commentary proved, but still a decent reflection of just how much this goal meant.

Fenerbahçe 2 Manchester City 1 (agg: 2-1)
(First round second leg 2 October 1968)

Roberto Mancini's greatest challenge at Manchester City is not to win the club's first trophy since 1976. It's not to coax anything resembling a smile from Carlos Tévez, or even to educate the English public in the joys of a turgid 0-0 draw away from home. It's to find a cure for Cityitis, the apparently incurable disease that afflicts the club.

Cityitis predisposes a proud club towards tragicomedy; it allows them to look a gift horse in the mouth while simultaneously shooting themselves in the foot. It damns their supporters with knowledge that, if something can go wrong for City, it will, and in the most shambolic manner imaginable. It's an endearing trait, but not exactly conducive to world domination

The term was coined by the former City manager Joe Royle, but it had been in evidence before he was even born. An early instance came in 1937-38, when City became the only English champions to be relegated the following season — and this despite them being the league's top-scorers. Other examples include Steve Lomas keeping the ball by the corner flag against Liverpool in 1995-96, even though City needed a goal to stay up, Jamie Pollock's absurd own goal that led to another relegation two years later, and Robbie Fowler missing an injury-time penalty that would have put City into the Uefa Cup.

And then there was their infamous first-round defeat to Fenerbahçe in City's only European Cup appearance to date. They had taken Manchester United's domestic title in 1968, and were confident of claiming their European crown the following season. Malcolm Allison, at that stage assistant manager to Joe Mercer, said City would "frighten the cowards of Europe".

Oh dear. Hubris and nemesis had been set on their familiar dance, and they were given an additional twirl before the tie when Mercer said he knew Fenerbahçe better than his own reserves — but then said he had never seen them play. They had conceded only 12 goals in 32 games while winning the league, a record that demanded respect, but Turkish football had no pedigree at this stage. Fenerbahçe had never been beyond the first round and had lost their nine away games in Europe. It wasn't exactly a banana skin.

Fenerbahçe employed the same tactics as modern-day City in the first leg, putting ten behind the ball and getting the 0-0 for which they came. City, playing their first-ever European game, went about their task with callow enthusiasm and were, as the Times put it, "trapped in the clever, deep web of the Fenerbahçe defence". Mercer, with the sort of generosity unimaginable in the modern age, admitted it had been "a moral victory for Fenerbahçe".

At least City knew they could do a lot better. Mike Summerbee had such a shocker that he could not even look his team-mates in the feet, never mind the eyes: he avoided the dressing-room after the game, preferring to find a hiding place and sit on his own.

There was nowhere for City to hide in the return leg. There were no 'Welcome To Hell' signs, and the players were treated warmly by locals in advance of the game, but during the match the scenes were similar to those that famously engulfed another Manchester club in Istanbul 25 years later, when Galatasaray put United out of the European Cup. In the Times, Geoffrey Green described "a fuselage of hissing rockets and drifting smoke reminiscent of some battlefield on the Western front… Seldom have I heard such a din or watched such a smouldering fever."

The match was, as the saying doesn't go, a game of two strikingly dissimilar 45-minute segments. Tony Coleman's early goal silenced the crowd for approximately 0.4 seconds, and City were very comfortable at half-time. "It looked for all the world," said the Guardian, "that Fenerbahçe were a beaten side."

But the substitute Abdullah Çevrim scored with his first touch after coming on at half-time, and from there it was all Fenerbahçe. City were ahead on the away-goals rule, but their backs were not so much against the wall as moulded into it. An absolute battering eventually brought a decisive strike from Ogün Altiparmak with 14 minutes remaining.

Ogün had been flown in from America, where he had been playing for the Washington Whips in the NASL, especially for the game. Losing to a team who had never won a tie before, and beaten by a man who had just stepped off a plane from America? In many ways, this defeat was pure City.

CSKA Sofia 2 Ajax 0 (agg: 2-1)
(Second round second leg 7 November 1973)

Stefan Mihailov is a strange kind of hero. For all bar a few seconds of his career, he was a nobody. If you saw him at a table of European Cup legends, you might be inclined to call security. Yet he certainly belongs there. Mihailov only ever scored one goal in Europe's premier competition, but it was one of the most important. It was the goal that, at club level at least, totalled Total Football.

Mihailov's goal, for CSKA in second round of the 1973-74 season, ended Ajax's dynasty. It also gave us the first sight of CSKA's gianticidal tendencies. Only Real Madrid and Juventus have put the holders out more often, but stories of hot superpower-on-superpower action are for a later issue. There were victories for CSKA over the defending champions Nottingham Forest and Liverpool in consecutive seasons at the start of the 1980s, yet their worthiest achievement was to end Ajax's run of three straight European Cups almost a decade earlier.

This was still a monstrously good Ajax side. Ten of the team that played CSKA had appeared in the final the previous season; six would start the World Cup final eight months later. They had beaten CSKA 6-1 on aggregate a year earlier. But in the summer they had lost two managers: Stefan Kovács had been replaced by George Knobel and, more damagingly, Johan Cruyff had taken his ball to Barcelona.

For all that, there seemed little to fear from CSKA. In the six years since reaching the European Cup semi-final they had won only three matches in Europe, against Haka, Partizani Tirana and Panathinaikos. The last of those had come in bizarre circumstances in the previous round. Both sides had won their home legs 2-1, with the match going to a penalty competition — during which, the referee made a hideous error and declared CSKA the winners when they led 3-2, with CSKA having two kicks left and Pana one. The match was replayed and CSKA cruised through.

Then they got down to the real business. They were beaten 1-0 in Amsterdam, with the goal scored by Jan Mulder, Cruyff's replacement. The scruffy and often filthy nature of the match — CSKA's keeper Stoyan Yordanov had his arm broken — suggested all was not well. Ajax, frustrated by their unusually coagulated football, embraced their darker side.

It's natural to assume that the hard man of a team is also its heartbeat, yet with Ajax that role fell to Cruyff, who was paternal even to those his senior. In times of trouble on the field, Ajax's players could spot Cruyff and know that everything would be okay. Without him, they looked around and saw only the fear in each other's eyes. That became even more acute when, in another grim struggle that Ajax's beautiful people struggled to comprehend, never mind deal with, Dimitar Marashliev's header took the game to extra-time.

Then came Mihailov's moment. He had been signed from the second division as cover for Petar Zhekov. He was approaching 30, and would soon return whence he came, having achieved nothing of note except this goal. He had only just come on the field when, with four minutes of extra-time remaining, he struck viciously past Heinz Stuy. Ajax appealed irrationally for offside, betraying their desperate confusion. Their era had ended. They would lose their domestic title to Feyenoord, and would not win the European Cup for another 22 years. They were never quite the same again. And nor — not that you would always know it — was the life of Stefan Mihailov.

Liverpool 3 Widzew Łódź 2 (agg: 3-4)
(Quarter-final second leg 16 March 1983)

Generalising about countries or regions is a dangerous thing these days, given the tedious number of woolly liberals keen wilfully to abuse the gift of political correctness in the name of a witchhunt. The fact remains, however, that in the days before football started in 1992, teams from the old Eastern Bloc were habitually described as "crack Eastern European outfits", and their unpronounceable names, inscrutable faces and otherworldly technique gave them a unique mystery and danger. It was almost sinister, like they had a computer chip inside them

Just ask Liverpool. During their remarkable spell of European dominance in the 1970s and 1980s, it was usually only when they went east that their hopes went west. Five of their six defeats in European competition came against sides from the old Eastern Bloc.

The last was in 1983, an odd but ultimately emphatic defeat by Poland's Widzew Łódź. While Łódź were a very handy side, they had lost probably their two best players, Zbigniew Boniek and Wladysław Żmuda, to Serie A after Poland's outstanding World Cup the previous summer. And they were coming off their winter break. Yet they eliminated Liverpool.

The aggregate score looks close, but Łódź led 4-1 — and with away-goal power to add — with 10 minutes of the second leg remaining. Quite how is anyone's guess, for the man of the tie was probably Łódź's outstanding goalkeeper Jósef Młynarczyk. His heroics enabled Łódź to win the first leg 2-0 despite Liverpool giving a display that their manager Bob Paisley called "as good as any we've given in Europe". Their first-half performance had been immaculate yet, as in their elimination by CSKA Sofia at the same stage a year earlier, Bruce Grobbelaar bore a significant part of the blame.

Against Sofia he completely missed a long cross, an error that resulted in a goal. This time, in the 49th minute, he cockily tried to claim a cross one-handed and instead dropped it at the feet of Mirosław Tłokiński, who did the rest. A drama turned into a crisis 10 minutes from time when, after a stunning surge from the left-back Andrzej Grebosz, the teenager Wiesńaw Wraga placed a supreme header into the corner from the edge of the area.

It was a classical European sting in a frenzied atmosphere that prompted a beautiful introduction from David Miller of the Times. "It is on nights such as this," he wrote, "in the fierce grip of an East European winter in which Napoleon went one down, when the elements and the natural theatre of the game conspire to create excitement which makes time stand still."

Łódź probably felt time was standing still in the early part of the second leg. At that stage, Liverpool had never overturned a two-goal first-leg deficit in Europe, but a glory night seemed likely when Phil Neal scored an early penalty. But Łódź held their nerve in the face of an onslaught from the Liverpool players and crowd — thousands had been locked out in what, in those days, was a rare midweek sell-out at Anfield — while continuing to threaten on the break.

Another mistake — this time, unthinkably, from Graeme Souness — led to Tłokiński's equaliser from the penalty spot, and when the excellent Włodzimierz Smolarek scored at the start of the second half Liverpool needed four. They got two in the last 11 minutes, but the game was up: Ian Rush scored and then David Hodgson scored a winner on the night that the Guardian said was "greeted almost with indifference".

The Kop made plenty of noise soon after, giving Łódź a typically generous ovation. Bob Paisley wasn't quite so munificent. He had been on edge throughout the tie — before the away leg he had bollocked Alan Hansen for drinking a cup of tea, because it had come from a Łódź official and could therefore have been "poisoned" — and bemoaned Łódź's "cry baby" attitude in the second leg. Still, his frustration was understandable. It was his last shot at a European trophy. Indeed, it was the end of an era in more ways than one. With Aston Villa going out to Juventus on the same night, England's attempt for a seventh successive European Cup was over.

Internazionale 1 Malmö 1 (aggregate: 1-2)
(First round second leg 27 September 1989)

There was one major English triumph in the European during the wilderness years of 1985 and 1990, even if it went almost completely unnoticed. In 1989-90, Roy Hodgson's Malmö caused a monstrous shock by putting Internazionale out in the first round.

Inter had won the title the previous season by 11 points — a staggering margin given the competitiveness of Serie A in the late 1980s and the fact that there were only two points for a win — and were full of players who would be integral to the best two sides at the 1990 World Cup, West Germany and Italy. In the summer, Inter had added Jürgen Klinsmann to a side that already contained Lothar Matthäus, Andreas Brehme, Walter Zenga, Giuseppe Bergomi, Ricardo Ferri, Nicola Berti and Aldo Serena.

The sides had previous, with Inter just sneaking past Malmö 2-1 on aggregate in the Uefa Cup a year earlier, yet few seriously envisaged a shock. Even when an excessively cautious Inter lost 1-0 in the first leg in Sweden, to a goal from Håkan Lindman in the 74th minute, there was little sense that Inter were in trouble.

Yet from the start of the second leg a fortnight later, it became apparent that something was in the air. Inter's nervousness betrayed a mindset where the fear of defeat was more powerful than the thrill of victory, and Malmö exacerbated that by taking the game to Inter from the start. They were a quintessential Swedish side: short on stars — a young Stefan Schwarz was one of only three players to appear at Italia 90 — but oozing purpose, teamwork and mental strength. Hodgson called them "a self-playing piano". For the most part, anyway. Jean-Paul Vondenburg briefly produced an ear-splitting riff in the 69th minute, when his hideous attempt to clear an awkwardly bouncing ball allowed Aldo Serena to stab under Jonnie Fedel and give Inter the lead.

With the aggregate score level, an assertion of the natural order seemed inevitable. Yet there was an almighty elephant in the stadium, the prospect of an away goal that would kill the tie stone dead, and nobody could ignore it when, in the 81st minute, Leif Enqvist headed Malmö level on the night.

It was a goal of daft simplicity: a floated near-post corner and a header from Enqvist, no more than three yards from goal as he smartly backed into his marker at the near post. Zenga should surely have come, but his inaction was a neat reflection of a night in which the gravity of the occasion had numbed Inter.

It was the only chance this great Inter side got at Europe's big prize, and in many ways they are a perfect advert for the cut-throat beauty of the old European Cup: they had to wait nine years for a fresh shot at the trophy, and they were out by the end of September.

Barcelona 2 CSKA Moscow 3 (agg: 3-4)
(Second round second leg 4 November 1992)

There is a delicious and rarely seen genre of European shock that loosely follows the narrative of a slow-burning horror movie. It starts sedately for the big side, who breeze along jauntily while getting a comfortable result in the first leg. But then, from nowhere, they suffer a Hitchcockian descent into trouble. A walk in the park becomes a desperate fight for survival, and usually there are no happy endings.

One of the best examples came in 1992-93, when Johan Cruyff's Barcelona suffered an unthinkable defeat to CSKA Moscow. It remains the only time in the Champions League era that the holders have been knocked out before Christmas. CSKA were not a great side — they subsequently failed to win a single match in a modest group with Marseille, Rangers and Brugge — but, as it so often the case with Russian sides, they clicked for a short, devastating spell of PlayStation football (or, rather, given that this was in 1992, Sensible Soccer).

The tie had started comfortably for Johan Cruyff's Barcelona. A 1-1 draw in Moscow, secured by Txiki Begiristain's equaliser, seemed to be more than enough. When Begiristain scored again to put Barcelona 2-0 up after half an hour of the second leg, coolly rounding Dmitry Kharine after a lovely through ball from Hristo Stoichkov, the job was apparently done. Indeed the muted celebration of that goal, and the first from Miguel Ángel Nadal, suggested that this was just a mundane day at the office for Barcelona. All they had to do was dot the 'I's, cross the 'T's and cross out the CSKA.

Sometimes, however, the box seat can get too comfortable. If Barcelona assumed they could just run the clock down, a nasty surprise awaited them. The timing of CSKA's first goal, lifted in off the bar by Yevgeni Bushmanov on the cusp of half-time after a forensic through-pass from Oleg Sergeyev, was crucial. As it marinated for the next 15 minutes, Barcelona had to contend with a fear that had not been there before; equally, CSKA had an unexpected shot of hope.

Barcelona were numbed into impotence, and there was a certain inevitability when the scandalously unmarked Denis Mashkarin plunged to head a left-wing corner past Andoni Zubizaretta in the 57th minute. Barcelona's nightmare was completed four minutes later when, from the excellent Sergeyev's precise cut-back, the substitute Dmitri Karsakov flicked the ball behind his standing leg and into the far corner.

Zubizaretta spread his arms limply, as if to ask what the hell was going on. Nobody had a clue, and the passage of time wouldn't make the result any more explicable. Cruyff's Dream Team continued to hoover up domestic titles, whereas CSKA finished ninth and tenth in the next two seasons. They won only one tie in any European competition in the next 12 years, and that was against Iprottabandalag Akranes of Iceland. As results go, this was the mother of all outliers.

AC Milan 1 Rosenborg 2 
(Group stage matchday six 4 December 1996)

The Champions League group stages were introduced to protect the big clubs from the tedious inconvenience of being legitimately eliminated by small teams, and to ensure they were still in the competition after Christmas. The tournament has largely achieved that, but that has at least served to imbue the increasingly infrequent shocks with a greater lustre. None more so than the first: Milan's failure to qualify for the knockout stages in 1996-97

Milan had reached the final in five of their last six European Cup campaigns, winning three. And though they stuttered through the group stages, losing twice to Porto, they only needed a draw from their final game at home to qualify. Given that they had won 4-1 in Norway, it didn't seem likely be too much trouble. Yet on a night of the long faces at the San Siro, a Milan side including Franco Baresi, Paolo Maldini, Billy Costacurta, Dejan Savićević and Roberto Baggio suffered one of their greatest humiliations.

Harald Brattbakk slammed a loose ball under Sebastiano Rossi to give Rosenborg the lead, but all was well with the world for Milan when Christophe Dugarry equalised in first-half injury-time. They remained one goal from elimination, however, and the second half was marked by such fear on the pitch and in the crowd that it was hard to work out which was the chicken and which the egg.

The fatalistic air was justified when Vegard Heggem scored the winner in the 70th minute after two appalling errors from Milan. First Zvonimir Boban's underhit pass went straight to Brattbakk on the halfway line; then Rossi lunged at Brattbakk's long cross like a wino trying to claim a stray balloon. He was nowhere near, and Heggem was able to head into the vacant net.

Milan, and the rest of Serie A, would become accustomed to such ignominy. Between 1996 and 2002, eight Italian sides went out of the Champions League before Christmas. By the end, their exits weren't a surprise at all. But the defeat that started Serie A's pre-millennium angst certainly was; and, with such shocks fewer and further between in the Champions League, it could be a long while before we see something to match Rosenborg's most famous night.