1) Ajax

For some clubs success always comes at a price they’d rather not have to pay. There’s always a catch. Borussia Dortmund might have enriched the soul with their freewheeling Champions League destruction of Real Madrid but their exploits are tinged with sadness, with the knowledge that what could be their greatest moment might not be the start of something great but an abrupt end to an era. Mario Götze has already agreed to join Bayern Munich at the end of the season, Manchester City are trying to woo Marco Reus and various suitors are batting their eyelids at Robert Lewandowski. If you can’t beat them, buy them.

Morals? Forget morals. It’s just business and, as they say, that’s all football is these days, which is why we cherish – and later mourn – the sides that spring up out of nowhere and capture our imagination, who make it possible for little guys everywhere to dream that it could be them one day. It is why people speak so wistfully about Ajax’s class of 95 and why they are always referenced in conversations about teams broken up before their time.

Ajax, the club of Rinus Michels and Johan Cruyff, are hardly the little guys in their own country. Yet outside of Holland, they shrink in comparison to the major European clubs, even though they have won more European Cups than Chelsea, Manchester United, Inter and Juventus.

Their last triumph was 18 years ago. But what a triumph it was, a victory for the shrewd management of Louis van Gaal and a fertile youth system that produced the likes of Edgar Davids, the De Boer brothers, Patrick Kluivert and Clarence Seedorf. There was a mixture of youth and experience, with veterans such as Danny Blind and Frank Rijkaard guiding the youngsters. They were decidedly Dutch, too; of the team that started the final against Milan in Vienna, there were only two foreigners in the starting XI, the Nigerian winger, Finidi George, and the legendary Finland striker, Jari Litmanen, while Nwankwo Kanu came off the bench.

This Ajax side were Champions League novices, having not appeared in the competition for four years. Yet despite being placed in the same group as Milan, who had thrashed Barcelona 4-0 in the previous season’s final, they were not overawed by Fabio Capello’s side. They beat them 2-0 home and away and even though they drew twice with Casino Salzburg, two wins over AEK Athens meant they finished unbeaten and top of the group.

From there, Ajax beat Hajduk Split 3-0 on aggregate in the last eight to set up a semi-final against Bayern, who were managed by Giovanni Trapattoni. The first leg in Munich finished 0-0 but it was back at the Olympic Stadium in Amsterdam where the tie really took off. At half-time the Dutch violinist, André Rieu, led the crowd in a rendition of the Second Waltz and on the pitch there was perfect harmony, too.

By the time Rieu took to the stage, Ajax were already 3-1 up. Litmanen had given them an early lead and although Marcel Witeczek equalised to briefly put Bayern in control, a crunching strike from Finidi quickly restored Ajax’s advantage, before Ronald de Boer opened up a two-goal lead. Litmanen swiftly made it 4-1 after the restart and although Mehmet Scholl pulled one back from the penalty spot, Marc Overmars capped off the evening by scoring a fifth with two minutes left.

On the same evening a 2-0 win for Milan against Paris Saint-Germain sealed their place in the final. Ajax had already beaten the European champions twice; now they had to do it when it mattered most and it felt appropriate that Kluivert, only 18, came off the bench to score the winner in the 85th minute.

Having also won the Dutch league, Ajax continued to flourish, despite the sale of Seedorf to Sampdoria for £1.5m and Rijkaard’s retirement. The following season they reached the final, where they were up against Italian opposition once again. This time, though, they were beaten on penalties by Juventus after a 1-1 draw. They retained their league title but the cracks were beginning to show; Overmars, for instance, missed most of the season and Holland’s miserable Euro 96 campaign with a bad knee injury.

The Bosman ruling was disastrous for Ajax. That summer Davids and Michael Reiziger both joined Milan on free transfers; Kluivert followed them to San Siro a year later. Inter signed Kanu for £1m. In 1997, Overmars left for Arsenal, playing a key role in their Double in the 1997-98 season. Although Ajax reached the semi-finals of the Champions League in 1997, losing to Juventus again, they slumped in the league, finishing fourth.

“The Bosman ruling means that not only do Ajax not get paid for some of the players they have nurtured since childhood, they now find Italian scouts haunting their youth team (Udinese recently signed a 19-year-old who had played only one game for the first team),” wrote David Winner in March 1997, shortly before Ajax beat Atlético Madrid in their European Cup quarter-final. “The loss of talent will continue this summer, starting with the brilliant but abrasive Van Gaal.

“Despite all their problems, Michael van Praag, the Ajax president, remains optimistic. ‘Every year one or two big names leave. It is sad, especially for me. But we are used to it. There is absolutely no panic,’ he said.

“Ajax’s annual budget is just over £20m, which the club is trying to increase to £100m. It is a lot for the Netherlands, but small by comparison with Europe’s giants. ‘In southern Europe, clubs can lose millions of dollars every year and still buy players because they get money from I don’t know where,’ Van Praag said. ‘We don’t think we will ever come to the same level as them budget-wise, but we try to narrow the gap. But we have something they do not have. Our school.’”

Noble, admirable intentions but the school has not been enough in a world where money rules. Since 1997, Ajax have reached the knock-out stages of the Champions League twice, losing in the last eight to Milan in 2003 and in the last-16 to Inter in 2006. In 1995, Ajax, the champions of Europe, beat Real Madrid home and away in their group; when they play them now, they’re lucky to get nil. JS

2) Red Star Belgrade

You might think that the winners of the worst European Cup final anybody can remember surrendered their right to misty-eyed what-ifs the moment that Ljubomir Petrovic instructed his players to return the ball to Marseille at any and every opportunity, for fear of being caught on the counterattack. (Even Sinisa Mihajlovic himself later admitted that it was “the most boring final match in European Cup history.”) You might, but you would be mistaken. The side that beat Marseille – having also beaten Bayern Munich in the semi-final after a sashaying run through the tournament – was the product of five years of team building: Ilija Najdoski, Darko Pancev, Miodrag Belodedici, Vladimir Jugovic, Dejan Savicevicćand Mihajlovic added to the 1988 league-winning squad already containing players such as Robert Prosinecki and Dragisa Binic (both signed in 1987) to give Red Star a league and cup double in 1990. The break up of the European Cup-winning side, in the midst of the disintegration of Yugoslavia, happened so quickly and so completely that within two years of the final the entire squad from that inglorious night in Bari, and the manager, were gone. Even by the time they contested the European Super Cup with the Cup Winners’ Cup winners, Manchester United, in November 1991, the team looked drastically different.

In Behind the Curtain: Football in Eastern Europe, Jonathan Wilson recalls a conversation with Stevan Stojanovic, the goalkeeper who joined Red Star in 1982 and who captained the side to the European Cup. “The tragedy is,” Stojanovic says, “we will never know how good we could have been.” In Mihajlovic’s version of events, Red Star sacrificed possession in the final not because they thought Marseille were better than them, but because of the differences in experience between the two sides. Marseille had been semi-finalists a year earlier, losing to Benfica on away goals, and reached the semi-finals of the Cup Winners’ Cup the year before that. Red Star were a younger side than the one that had taken Real Madrid so close in the 1986-87 quarter-finals, a “squad full of 21, 22 and 23-year-old kids”, as Mihajlovic put it. They were on the brink of greatness and could not afford to find out how well they might cope with having to come from behind in the club’s first European Cup final; why should they trouble themselves with aesthetics?

It was not as if they had not proved themselves over the course of the competition. In the first round, after a 1-1 home draw, Red Star clobbered Grasshoppers 4-1 away from home – a match watched by Walter Smith, scouting for second-round opponents Rangers, whose report back to the manager Graeme Souness was famously brief: “We’re fucked.” Rangers duly travelled to Belgrade and took a 3-0 hiding, rendering their second-leg match a formality. “Graeme Souness and his team retreated last night with tails tucked firmly between their legs,” wrote Joe Lovejoy in the Independent, “uncomfortably aware that if the Yugoslavs’ finishing had done justice to their technical expertise or had Chris Woods not been in heroic form, emphatic defeat would have become dire humiliation.” Red Star’s 6-0 aggregate quarter-final win over Dynamo Dresden is asterixed by the second-leg walkover forced by fan violence, but with little of the match remaining the Yugoslavs were on course for a 5-1 aggregate victory in any case. The first leg was over as a competition before an hour was up, with Prosinecki and Savicevic orchestrating things. All of the other potential semi-finalists – including Bayern, Porto, Spartak Moscow, Real Madrid, Milan and Marseille – wanted to avoid Red Star.

Bayern were the ones to draw the short straw, falling to a 2-1 home defeat in the first leg despite taking the lead through Roland Wohlfarth midway through the second half. A trademark left-footed free-kick from Mihajlovic extended Red Star’s lead in the second leg, in front of an 80,000-strong crowd at the Marakana, but Klaus Augenthaler and Manfred Bender levelled the scores in the second half. With extra-time looming, Augenthaler deflected a Mihajlovic ball past his own keeper to put Red Star through in the 90th minute. The trial of this match arguably fed in to Petrovic’s gameplan for the final against Chris Waddle’s Marseille, who had relatively little trouble seeing off Spartak Moscow in the other semi-final. There was also the small distraction of near-war at home – as one supporter put it, a win in the final would permit them to “live normally for another three days.” Though the end of the tournament was hugely anticlimactic, we should not forget the context, nor the glorious counterattacking football that Red Star had played up to that point: fast, powerful, unpredictable. Savicevic, popping up on both wings and just as difficult to handle on each, finished second in the voting for that season’s Ballon d’Or.

The loss, eventually, of Savicevic, and others much sooner, was sadly inevitable; Yugoslav players left the league in droves as their earnings plummeted and the country was consumed by conflict. A gaggle of scouts took up seats at the final to watch Red Star’s key players, and though “they kept their gifts well hidden”, as David Lacey put it in the Guardian’s report, Prosinecki joined Real Madrid that summer, while Binic, signed only a year earlier, joined Slavia Prague. Stojanovic went to Royal Antwerp; the defender Refik Sabanadzovic to AEK Athens; Slobodan Marovic to Norrkoping. Still Red Star retained the Yugoslav First League title the following season, Pancev scoring 25 goals to outstrip Partizan, but come the following summer he too was gone, to Internazionale. Indeed, Serie A was a particular beneficiary of the breakdown of the Yugoslav league in 1992: Savicevic signed to Milan, Jugovic joined Sampdoria, and Mihajlovic went to Roma. Belodedici made off in the direction of La Liga and Valencia, while Najdoski joined Real Valladolid. GT

3) Leeds United

The story of David O’Leary’s Leeds United “babies” is a story of optimism, youthful verve, hubris, violence, profligacy and financial nemesis. It is also the story of three teams and three managers with rival claims to paternity – Howard Wilkinson, the author of the 10-year plan in 1988 that brought promotion and the title to Elland Road, George Graham who took over in the autumn of 1996 and O’Leary, Graham’s assistant, who abandoned his predecessor’s caution and placed his trust in the outstanding graduates of the 1997 FA Youth Cup winning side.

Wilkinson deserves the credit for establishing the system and designing the facilities that nurtured Paul Robinson, Harry Kewell, Stephen McPhail, Matthew Jones, Alan Smith and Jonathan Woodgate and for buying Nigel Martyn and Lee Bowyer, Graham for recognising Lucas Radebe’s leadership qualities and upgrading at centre-forward from the still crafty if physically antiquated Ian Rush to the thrillingly dynamic Jimmy Floyd Hasselbaink. O’Leary then blooded Leeds’s youngsters, most notably introducing Smith off the bench at Anfield to score with a carefree swank, and strengthened, at first, astutely. He knew how to tickle the support, making David Batty’s return his first priority, then followed it with Eirik Bakke and used some of the £12m Leeds reluctantly accepted for the sale of Hasselbaink to buy Michael Bridges, who had an outstanding first season as Leeds finished in third and secured a Champions League qualifying tie.

Mark Viduka, Olivier Dacourt and Dominic Matteo were all signed in the summer of 2000 for the Champions League campaign and, when Kewell and Bridges were injured, Robbie Keane joined on loan. After making it through the first Champions League group round despite an opening-tie walloping by Barcelona, Leeds were bullish enough to pay West Ham United £18m for Rio Ferdinand who was immediately appointed captain.

It was only after Christmas that their league form clicked but in Europe they made it all the way to the semi-final, memorably defeating Lazio with a glorious Smith goal set up by Viduka’s delicate backheel, overwhelming Anderlecht in Brussels and destroying Deportivo La Coruña in the quarter-final at Elland Road before just surviving when the tables were turned in the second leg. Valencia won the semi-final convincingly enough and Leeds missed out on Champions League qualification by a point, still seething that a Wes Brown own goal in a 1-1 draw with Manchester United had been unreasonably disallowed. Twelve years on those fine margins, which could have made the difference to a reckless gamble paying off or leading to a dozen years of purgatory, still rankle. In truth, though, Peter Ridsdale’s most ridiculous decision was his next one, borrowing £60m in a bond and using part of it to pay Inter £12m for Keane, Derby £7m for Seth Johnson and Liverpool £11m for Robbie Fowler. This wasn’t so much going all-in as putting all your possessions and your very life on the line. And, as we know, it failed.

Top of the Premier League on New Year’s Day 2002, Leeds slumped alarmingly after defeat by Cardiff in the FA Cup and finished fifth with a dressing room acrimoniously torn over O’Leary’s book “Leeds United on Trial” whose title cashed in on the notoriety of the prosecution of Woodgate and Bowyer for affray and assault. Out went O’Leary and in came Terry Venables, Leeds selling Ferdinand for £30m in the summer to give them breathing space before panicking after Christmas and essentially paying Fowler to go. Newcastle exploited Leeds’s desperation and bought Woodgate on the cheap, Kewell left for Liverpool at the end of the season and took a slice of the fee too before relegation the following season ushered on imminent financial catastrophe and the exodus of the remaining players for negligible sums.

It has been portrayed as an Icarus-like football fable. Ambition took Leeds too close to the sun and those final purchases seared the wax. The fact is, though, as Wilkinson knew, Leeds never had the income to compete with Manchester United in the Premier League and did not have a wealthy benefactor to give it to them. So he tried to emulate them by producing his own players – and the spine of the team that won qualification to the Champions League in 2000 was his legacy. With careful husbandry and targeted investment it could have matured into a great one. But a dash for growth stimulated the board more than Wilkinson’s sustainable model and demolished the club’s credit-worthiness and credibility. The severely diminished club that remains is still paying the price. RB

4) Parma

Parallel parking when people are looking. Public speaking. Running a marathon. Maintaining eye contact with the opposite sex. Maintaining eye contact with Roy Keane. These are all intimidating things to do. But none of them are anything like as intimidating as Serie A in the 90s.

It was a league brimming over with talent. Juventus, Inter and Milan were naturally at the top of the food chain, but you had to take Roma and Lazio into account. Fiorentina had Gabriel Batistuta and Manuel Rui Costa. Sampdoria, Champions League finalists in 1992, had Roberto Mancini. And then there was Parma. It is probably not a name that will make younger people go weak at the knees. On a wider scale, Parma are largely inconsequential these days. But not then.

Until their promotion to Serie A under Nevio Scala in 1990, they had spent much of their existence scrabbling around the lower divisions. Once they were in the top flight, though, the investment began, with the club backed by Calisto Tanzi’s food company, Parmalat. In 1992, they won their first major honour, beating Juventus 2-1 on aggregate in the final of the Coppa Italia and a year later they beat Royal Antwerp 3-1 in the final of the Cup Winners’ Cup. They were on the map and it was a major surprise when they failed to retain their trophy a year later, beaten 1-0 by Arsenal in the final.

Not to worry. With one European trophy under their belt, another soon followed as Juventus were prevented from adding the Uefa Cup to their league title in 1995. Parma had finished 10 points behind Marcello Lippi’s side in the league, but won the first leg of the final 1-0 at home thanks to Dino Baggio’s goal and then drew 1-1 in Turin, Baggio grabbing the vital goal again after Gianluca Vialli had put Juventus in front.

For all their success in the cups, they could not quite crack the league though. They finished sixth in 1996 and Scala was replaced by Carlo Ancelotti but the emergence of Gianluigi Buffon and the arrivals of Lilian Thuram, Enrico Chiesa and Hernan Crespo that summer helped Parma maintain a title bid that ultimately ended in frustration.

With three games left, they needed to beat Juventus to keep their hopes alive but although they took the lead through Zinedine Zidane’s own goal, a highly contentious penalty from Nicola Amoruso was enough for Lippi’s men. Although Juve drew their final two games and Parma won theirs, Ancelotti’s side missed out by two points.

The spending continued. In came the Argentinians, Juan Sebastián Verón and Ariel Ortega. A second Uefa Cup followed in 1999 with Marseille beaten 3-0 in the final. Yet it was unsustainable and by the turn of the century, the exodus had begun. In the space of a couple of years, Parma lost the likes of Buffon, Fabio Cannavaro, Thuram, Crespo, Baggio, Ortega and Verón, and in 2004 the club was declared insolvent after Parmalat went bankrupt following fraud by Tanzi, who was sentenced to 18 years in jail in 2010. Parma’s glory years are a mere memory now. JS

5) Porto

Evolution is not really José Mourinho’s style. On his appointment in early 2002 he promised to take Porto, struggling to keep pace with the league leaders, immediately back to championship form. “From here,” he said in a letter in which he welcomed the squad to Porto, rather than the other way around, “each practice, each game, each minute of your social life must centre on the aim of being champions.” Having lifted the team to third in a few months (after January they lost only two matches), Mourinho set about constructing the side that would win the treble: Nuno Valente and Derlei, who played under him at União de Leiria; Benfica cast-off Maniche (as well as Edgaras Jankauskas); Paolo Ferreira, playing on the right for Vitória de Setúbal, would become a flying full-back. He also brought Jorge Costa back into the squad, where Ricardo Carvalho, Deco and Costinha were already central to the new manager’s plans.

This team would take some beating: aggressive, fast-thinking – and, crucially, well organised. It was not until mid-February of the 2002-03 season that Porto were beaten in the league, in fact, tripped up by a trip to Maritimo. Three months later Pacos Ferreira enjoyed a 1-0 win over Porto, but no one could take three points from Estádio do Dragão – only Belenenses took even one, on the first day of the season. Porto finished champions ahead of Benfica, 11 points clear at the top and not put off their stride by a successful Uefa Cup campaign. New signings worked – Derlei was the Uefa Cup’s top scorer, and the old worked in ways anew; after the final, a fraught win over Celtic, Kevin McCarra wrote in the Guardian: “Deco has turned into a a creator of the highest calibre.”

The following season Porto were just as successful in the league, losing only twice – both as the season wore on and both ahead of Champions League second legs. Their home remained a fortress, save for a group-stage defeat to Real Madrid. In the knockout stages of the Champions League, Manchester United, Lyon and Deportivo fell before the final against Monaco, another side on an upward trajectory that would soon lose Jérôme Rothen, Ludovic Giuly and loanees Hugo Ibarra, Édouard Cissé, and Fernando Morientes. “Mourinho, an artist of strategy, destroyed Didier Deschamps’s team with his canny adjustments,” read the Guardian’s report, reflecting on the switch of Dmitri Alenitchev in place of Carlos Alberto. “It was a subtle and lethal switch to counterattacking means.”

Porto won virtually everything they could have done in two-and-a-half-seasons under Mourinho; wondering what might have been probably seems a smidge perverse. What do you mean, what might have been? They won everything! Two league titles, the Portuguese Cup, the Portuguese SuperCup, the Uefa Cup and the Champions League. And they have kept on winning the league in Mourinho’s wake, as well as domestic cups aplenty. But we’re perhaps entitled to wonder what sort of European dominance Porto might have mustered had Mourinho not been out the door the second the 2003-04 Champions League title was won (Carvalho and Ferreira following him to Chelsea and Deco heading for Barcelona); he has, after all, taken his club to a semi-final or better in six of the nine seasons since. GT

6) Bayer Leverkusen

If you were to ask the BBC sound department for an accompaniment to the end of Leverkusen’s 2001-02 season, they would probably dig out a heavily worn tape from Some Mothers Do ‘Ave ‘Em. Something with enough crash-bang-screeching-cat to convey the calamity of the late-season defeats that allowed Borussia Dortmund to nab top spot in the Bundesliga; the defeat to Schalke in the German Cup final; the more predictable (Ze Roberto was suspended and Jens Nowotny was injured) but no less painful loss to Real Madrid in the Champions League final.

The collapse of Leverkusen’s aspirations tends to define the story but this was a superb side: Michael Ballack and Yildiray Basturk operating in perfect tandem in central midfield while Ze Roberto and Bernd Schneider probed out wide. Oliver Neuville was just about as clever a lone striker as you could find. Klaus Toppmöller gave his backline flexibility in numbers by playing Carsten Ramelow just in front of central defence, dropping in whenever those behind him fancied a foray forward. “We only have a small squad, but whoever comes in is infected by the euphoria which surrounds us,” Ballack told reporters ahead of the Champions League final, but the feelgood factor took a hit when the end of the season arrived with no silverware. Ballack left for Bayern Munich, as did Ze Roberto, instantly robbing the side of impetus – Ballack was the club’s top scorer with 17 league goals in 2001-02. The team only just avoided relegation the following season, midway through which Toppmöller was sacked, and other members of the Champions League final team gradually drifted away: Boris Zivkovic and Thomas Brdaric in 2003, and Basturk and Neuville in 2004. GT

• With thanks to Rob Holmes