IT WAS 14 SEPTEMBER 1994 and Ajax were up against AC Milan. Never before or since had a single football match transversed generations with such poignancy and awe. Under a pregnant Dutch sky, an archaic, city-centre stadium hosted 21st-century football in a 20th-century setting. Naturally, the poignancy is a recent burden, heightened by a stuttering transition from European kings to selling clubs. An often painful transition two decades in the making.

Back in 1994, with the Champions League in the infancy of a remodelling, elements of the occasion were recognisably modern. The logo, the anthem, and the heightened sense of corporate-fuelled pomp and ceremony were present, yet Bobby Haarms sat chain smoking in a primitive dugout. Not a sponsor-embroidered, leather car seat in sight. Past and present were merged beautifully.

On a rain-sodden and muddy pitch, regrettably yet sensibly a thing of elite football’s past, two European heavyweights collided. Youthful artistry faced established and esteemed legends. In the dugouts, 48-year-old Fabio Capello and 43-year-old Louis van Gaal were at their cocksure and preening best.

The 1994-95 Champions League season is rightfully etched into football’s collective memory for its final. Ajax’s youthful team sent from the Gods, clad in distinctive deep purple, and confirming something of a power shift in European football, defeated and stunned AC Milan 1-0. However, their often-forgotten group stage meeting at the Olympisch Stadion in Amsterdam proved equally memorable. Unlike the final seven months later, it was a match with no history, no precedent, and little in the way of Dutch expectation.

Casting aside Ajax’s 1992 UEFA Cup title, recent continental success had been hard to come by. Thirteen years had passed since the Dutch club had progressed beyond the European Cup first round. Milan, by contrast, had made the European Cup final in four of the previous five seasons, winning on three occasions, the most recent coming against none other than Johan Cruyff’s Barcelona Dream Team.

The group stage encounter set van Gaal’s upstarts on the road to European dominance. Already stylish rulers of the roost domestically, locking horns with the might of Milan paved Ajax’s way to two successive Champions League finals.

If the modern era’s first round of Champions League group games have become predictably careful affairs, one could be forgiven for thinking this one was a final. For the sanguine van Gaal, it was by design. His line-up, formation and, dare we say, philosophy would become fabled.

Ajax of the mid-1990s were the epitome of a bold, attacking 3-5-2, or 3-4-3, or 3-1-2-3-1. Like all art forms, Ajax’s tactics were open to interpretation. Van Gaal had his side laced with an echt Amsterdamse swagger, and a stubborn if yet unrealised confidence. Despite their domestic success, Ajax’s surefootedness was an audacious approach against the giants of Milan.

Read | The Ajax utopia under Louis van Gaal

Despite the club’s apparent gulf in European pedigree, there was more than a degree of familiarity between players and coaches. As the teams lined up in a small and dingy tunnel, Frank Rijkaard, who had transferred back to Ajax from Milan in 1993, received an uncharacteristically warm embrace from Fabio Capello. Ruud Gullit, more than familiar to most of the Ajax team, was in his second spell with Milan, and the last remaining of their famous Dutch trio.

Along with generous rainfall, the evening air carried a fervent atmosphere. A sell-out crowd lent vocal support to Freddie Mercury as ‘We Are the Champions’ was belted out of a dated loudspeaker system. Perhaps a tip of the hat to the reigning European champions, or to the unexpected champions-elect.

On the playing surface, puddles formed and reflected the glow of several flares.

Metronomically blending youth with experience and tactical discipline with fluidity, van Gaal’s Ajax were the perfect storm. The back three of Danny Blind, Frank de Boer and Michael Reiziger offered defensive steel and transitional fluidity. Blind, with poise and experience locked into every tight curl on his head, was the kingpin. De Boer and Reiziger intelligently covered space, filled in as central defenders when needed, and intelligently fed the midfield.

Rijkaard’s intelligent versatility just ahead was crucial. At the prime of his playing intellect, and with ageing legs comfortably covered by those around him, Rijkaard was constantly three passes ahead.

With emphasis placed firmly in the attack, natural width and alarming pace came in the form of Marc Overmars and Finidi George in the final third. The presence of Rijkaard dropping into defence meant de Boer and Reiziger could easily switch their roles of central defenders or supporting wing-backs.

Tactical discipline came in midfield. Showing positional intelligence, and impressive obedience for his tender years, Edgar Davids accompanied Rijkaard in various holding roles. With strict instructions not to overtake Overmars and George in front, Ronald de Boer complemented Davids and Rijkaard. All three were crucial in Ajax’s ability to attack from all over the pitch and offensively swarm the opposition.

In something of a wizard and apprentice duo, Ajax’s front two of Jari Litmanen and 18-year-old Patrick Kluivert provided everything the enlightened European football fan could ever want from a strike force.

Much has been made of the youthfulness of van Gaal’ Ajax, and rightly so. Momentarily removing Rijkaard and Blind from the equation, the average age of Ajax’s starting 11 was a staggering 22. Adding the experienced defenders, that number only increases to 24.

Read | Fabio Capello and the legendary Milan years

By contrast, the average age of the Milan team was four years senior. Even with the decorated abundance of Franco Baresi’s experience wrapped in the captain’s armband, seniority was made to count for little.

While it should be recognised that the Italian’s had Alessandro Costacurta, Cristian Panucci, Marcel Desailly, Demitri Albertini, Marco Simone and Daniele Massaro all injured or suspended, nothing should be taken away from the perfection witnessed in Ajax colours. Milan’s starting line-up still included the aforementioned Baresi and Gullit, in addition to Paolo Maldini, Zvonimir Boban, Roberto Donadoni, and Dejan Savićević.

Ajax dominated the first half. Gullit, playing in an advanced role perhaps beyond his 31 years, was alienated. Ajax combined tactical artistry with dogged tenacity and came closest to breaking the deadlock through Kluivert and Davids.

The opening goal came five minutes into the second half when Ronald de Boer cut a deft finish over the top of an advancing Sebastiano Rossi. De Boer picked the ball up deep and started and finished the move via intelligent movement and a neat one-two with Kluivert.

Finidi George came agonisingly close to doubling the advantage a few moments later. With some high pressing to have Jürgen Klopp’s mouth watering, Davids snapped into a block, and George steamrollered onto the loose ball. His shot shaving the post with Rossi beaten.

In the shadows of the glare and hue of the Olympisch Stadion’s aged floodlights, the Amsterdamse crowd hit fever pitch. Sensing a scalp and a statement of intent, they bayed for more. Naturally, they weren’t waiting long.

Jari Litmanen, who had somehow been dancing, twisting and turning the ball through what was fast becoming a quagmire, smashed home the second on 64 minutes. Like de Boer for the first, and evidencing the relentless fluidity of Ajax, Litmanen started and finished the decisive move.

Allowed space in the middle, Litmanen advanced, teased, prized and fed Overmars to the left. After making light work of stand-in full-back Stefano Nava, Overmars whipped a deceptive cross which just about evaded Baresi, and everyone other than Litmanen. Already falling backwards, the sublime control and power generated on the half-volley epitomised Litmanen’s subtle skill set. His connection perfect, Rossi beaten.

Read | How Amsterdam changed the world of football forever

“Twee nul!” The tone of audacious surprise in the voice of Dutch commentator, Eddy Poelmann, is almost heart warming.

Overmars himself came close to adding a third 10 minutes before the end. In showcasing the aggressive, precise and purposeful transitions through the lines, the move started with a Milan corner. Savićević received a short corner and immediately fell victim to a perfect sliding tackle celebrated like a goal. Ronald de Boer picked up the charge, fed Litmanen, who steadied himself, before feeding Overmars, who sliced wide from a tight angle. Defence to attack in 3.2 seconds.

The following day’s de Volkskrant heralded the “strong-willed Ajax” and proclaimed “a direct hit to Milan’s crown of invincibility”.

For Amsterdammers there is rightful romance in recalling football at the Olympisch Stadion. It should, of course, be noted that the Gezellig venue played host to European football for another 18 months after the Milan match. AEK Athens, Hajduk Split and Bayern Munich were all defeated en route to the 1995 final in Vienna. The latter, a storming 5-2 win over Giovanni Trapattoni’s German champions, featured a rousing half-time performance by Dutch violinist André Rieu.

With the Amsterdam ArenA edging closer to completion, Ajax returned to the Olympisch Stadion to defend their European crown the following season. A group stage victory against Real Madrid kicked off an impressive campaign, and home wins followed against Grasshopper, Ferencváros and Borussia Dortmund. Despite losing the semi-final home leg to Panathinaikos, Ajax recovered to win emphatically in Greece. Against Juventus in the final, it took extra-time and penalties to condemn Ajax to a somewhat unfortunate defeat.

However, despite witnessing seven further victories en route to successive finals, no occasion quite matched the September 1994 encounter with Milan. It was a full throttle, romantic, European glory night under rain and flood lights in central Amsterdam, and it was the last of its kind.

Ajax moved into the ArenA in the summer of 1996. A modern 53,000 capacity home fit for all occasions, yet it’s out-of-town location and perceived lack of homely atmosphere see that it’s a bond of modern necessity rather than true love. Though the stadium has played host to no fewer than 15 Champions League campaigns in its 20-year history, they have all been rather short lived and unspectacular.

By 1997, and in addition to losing their spiritual home, Ajax’s dream team was decimated, largely thanks to the Bosman ruling and lucrative offerings of football in Italy, Spain and England’s blossoming Premier League. By 1998, only substitute goalkeeper Fred Grim remained from van Gaal’s squad.

That same year, the Olympisch Stadion was stripped of it’s ugly 1937 football-sponsored extension, and lovingly restored to its original 1927 design. Regrettably for Ajax, anything regarding full restoration to their brilliant best appears little more than a pipe dream.

By Glenn Billingham @glennbills