Cruyff to Van Gaal to De Boer: Can Ajax rejoin Europe's elite?

May 24, 1995 will forever be a date etched in the Ajax annals as the Dutch club claimed their fourth European Cup title.

In what was an epic conclusion to a memorable season – and in the case of Frank Rijkaard, a career – Louis van Gaal joined the illustrious names of Rinus Michels and Ștefan Kovács by leading Ajax to glory in Europe’s most prestigious club competition.

As this year's Champions League proper rolls into action next week, 1995 Ajax alumnus Frank de Boer is in the managerial hot seat – but expectations are no longer what they were.

That victorious campaign had been Ajax's first tilt at the European Cup since 1985/86, when they had been eliminated by FC Porto 2-0 over two legs in the first round. Johan Cruyff was the coach back then and despite that setback he wouldn’t wait long to bring European silverware back to Amsterdam.

The following season Cruyff guided Ajax to their first (and only) Cup Winners’ Cup triumph, defeating Lokomotive Leipzig in Athens with a goal from Marco van Basten. But the star striker was then sold to AC Milan and a disappointed Cruyff left for Barcelona.

Cruyff’s lasting legacy at Ajax was his blueprint of how the modern side should play. Incorporating many of the ideals he shared with his mentor Michels during the time he was a player, he devised a 3-3-1-3 formation which allowed his side to dominate possession with a fluid passing game. It wasn’t enough to win the league from Guus Hiddink’s all-conquering PSV Eindhoven, but it would serve his successor well.

Unlike Cruyff, Louis van Gaal didn’t have a stellar playing career: despite coming through Ajax’s academy he couldn’t break into the senior team, leaving to play much of his football at Sparta Rotterdam.

He did however return to Ajax as Leo Beenhakker's assistant, and when ‘Don Leo’ left after guiding Ajax to Eredivisie glory in 1990 – ending a five-year wait for the domestic title – Van Gaal was appointed manager.

VAN GAAL: SAME FORMATION, NEW PLAYERSVan Gaal would continue the 3-3-1-3 system – but had difficulty turning around a hostile pro-Cruyff crowd, especially when results weren’t going his way. In reality, the club were at a crossroads. Some of the squad were either stagnating or coming towards their sell-by date.

After Ajax beat Torino in the 1992 UEFA Cup Final, winger John van't Schip moved to Genoa. Over the next couple of seasons he was followed through the door by Inter-bound Wim Jonk and Dennis Bergkamp, winger Bryan Roy (to Foggia), striker Stefan Pettersson (returning to FK Gothenborg), defender Michel Kreek (to Padova) and goalkeeper Stanley Menzo to PSV.

Van Gaal wisely kept a strong central spine of Frank and Ronald de Boer, Danny Blind and Edwin van der Sar, but Ajax needed an injection of youth – and just as Alex Ferguson would prove over the English Channel, if you're good enough you're old enough.

Patrick Kluivert, Jari Litmanen, Marc Overmars, Edgar Davids, Clarence Seedorf and Michael Reiziger came into the side with the intelligence of the Ajax academy allied to the impetuous fearlessness of youth.

Litmanen spent 1992/93 as understudy to Bergkamp, impressing enough when the No.10 was injured to replace him permanently when the Dutchman joined Inter. His league-topping 26 goals the following season helped Ajax win the league and returned European Cup football to the Dutch capital.

The 1994/95 Champions League group campaign couldn’t have had a more daunting start: the visit of reigning champions AC Milan, who four months earlier had demolished Cruyff’s Barcelona ‘Dream Team’ 4-0 in the Athens final. But Fabio Capello’s men were rudely awakened as fearless Ajax ran out 2-0 winners with goals from Ronald de Boer and Litmanen.

Ajax had sent a message to Europe and continued as they had started. Casino Salzburg held them to two draws but AEK Athens were defeated home and away and Van Gaal's men completed a memorable double over Milan to top the group.

In the quarter-finals, Ajax got a goalless draw at Hajduk Split and overpowered the Croatians 3-0 at home, thanks in part to a peach of a free-kick from Frank de Boer. In the semis, another 0-0 at Bayern Munich set up a memorable 5-2 home win and a final showdown with Milan again.

In the Vienna final, Kluivert – the 18-year-old who had only made his Ajax debut the previous August, and who often rotated with Nwankwo Kanu as the No.9 – came off the bench to score what proved to be his most memorable goal.

DE BOER: THE SAME BUT DIFFERENT The modern Ajax don’t have a Kluivert; as a manager, Frank de Boer can't call upon the same calibre of playing talent available to Louis van Gaal all those years ago.

The financial realpolitik of modern football means that the game today is a universe away from the mid-90s, when Ajax followed their Champions League triumph by reaching the final again, losing to Juventus on penalties before the Bosman ruling allowed most of their stars to walk away for free as the club slid into mediocrity.

Along the way to that second successive final they humbled Real Madrid in front of a sell-out Bernabéu. They return to the Spanish capital in three weeks' time, but you'd get long odds on a repeat away win: last November, Madrid humbled Ajax 4-0 in Amsterdam.

Although compared to last season there’s renewed optimism of making it through the group, De Boer concedes that Real Madrid are in a class of their own and should win a group which also includes Lyon and Dinamo Zagreb. Ajax progressing isn’t impossible, even if it looks difficult.

De Boer shares much of his tactical vision with Van Gaal: he even prepares for games in a similar fashion. His changes have been subtle but have had impact: compared to 12 months ago under Martin Jol there’s a huge contrast in the way Ajax play. And it works, judging by last season's league title.

To an extent, methods of coaching and training have returned to the days of Van Gaal, with a strong emphasis on individual coaching. Cruyff – now commissioner at the club, his first official position at the club since his departure as coach nearly 25 years ago – had recently lambasted the new modern methods of being dependent on machines.

Though yet to adopt the 3-3-1-3 system favoured by Cruyff and Van Gaal, De Boer recalled after watching FC Barcelona play three at the back against Villarreal how he fell in love with the formation – while stopping short of hinting whether he’ll return it to the club.

It's 15 years since Ajax reached a European final; a generation has grown up regarding the club who Jorge Valdano said "approached football utopia" as little more than a sleeping giant. Returning a degree of respectability and pride to Ajax – especially in Europe – remains De Boer's ultimate goal, as well as playing the brand of football he enjoyed at the club.

Still in the first year of his full managerial career, De Boer has already earned the praise of Van Gaal, Cruyff and even Hiddink – who cryptically called the Ajax man his "successor". Across in Spain, where he played five seasons with Barcelona, he’s been dubbed the "Dutch Guardiola" – a comparison he brushes off, saying he’s yet to reach his former team-mate’s level. However, he  agrees that what Pep is doing he aspires to replicate, given their shared beliefs.

If Ajax do reach the Munich final and win their fifth European Cup, De Boer will become the first man to win the trophy in his début season as both player and coach. Stranger things have happened.