Standing in their way in Rome were Van Gaal’s reigning European champions. As well as winning the UEFA Super Cup and obliterating their rivals in the Eredivisie in 1995-96, the likes of Van der Sar, Jari Litmanen, Patrick Kluivert, Edgar Davids, Danny Blind and the De Boer brothers strolled through another dominant European run, failing to win on just two occasions en route to the Italian capital.
Juve were well aware of the challenge they were up against, with Sergio Porrini highlighting Litmanen as the main threat.
"He was undoubtedly the most dangerous, he was in a moment when if he touched the ball he scored. And in fact he did. The wingers in that 4-3-3 were also very good, the Dutchman Kiki Musampa and the Nigerian Finidi George, who could cause damage in attack but at the same time concede a lot in defence."
However, Ajax’s youthful exuberance had by now turned into hubris, with Van Gaal providing their opponents with extra motivation.
As Ciro Ferrara said: "A few days before the final, in fact, when asked who would win the Champions League, Ajax manager Van Gaal replied: 'I don't know who will win, but I know that cup will be returning on our plane.'"
The Italian added: "That spark gave us the push we needed."
Firing his players up with an improvised speech, Lippi sent them out with the message: "Nine times out of 10, they win, but one damn time it's our turn. And this is the night."
His words took immediate effect. Just 12 minutes into the final, Frank de Boer misjudged a header and waited for Van der Sar to rush out and grab the ball, but Ravanelli nipped in to steal it and poke into the empty net.
Ajax responded well, though, and Porrini’s words proved prophetic when De Boer’s free-kick was parried by goalkeeper Angelo Peruzzi into the path of Litmanen who fought off a defender and scooped home from close range.
Neither side could break the deadlock across the remainder of the 120 minutes of intense football and it eventually came down to a penalty shootout.
Gianluca Vialli, according to Lippi, refused to take one of the early spot-kicks, haunted by ghosts at the same stadium while representing Italy at the World Cup.
"At the Olimpico I had missed a penalty in the 1990 World Cup against the United States, and I had broken my foot taking another against Roma," he told Corriere della Sera, explaining why he wanted to take the fifth or sixth penalty. "That night I knew it was my last chance to win the Champions League.
"Imagine the nightmares, otherwise!"
Lippi explained: "Vialli had the negative feelings of the final against Barcelona and he cared particularly about that final. He told me: 'I care so much about this Champions League that if we were to lose because I missed the penalty I would commit suicide'."
A similar situation was going on at Ajax, as Sonny Silooy admitted: "None of us wanted to take a penalty after extra time. I was really bummed about that. Louis had gone around to everyone. Key players ran away from it."
While Ferrara, Gianluca Pessotto and Padovano converted their kicks, goalkeeper Peruzzi produced the heroics between the posts. He palmed away Davids' opening attempt - later laughing that the midfielder "shot it right at me!" - before diving to deny Sonny Silooy.
At 3-2, the stage was set for Jugovic to step up.
His team-mates were nervous and the directors in the stands couldn’t bear to watch, but Jugovic was smiling. The outcome had already been decided, he sensed.
"I was certain I would score; I was smiling because destiny had chosen me for such an important victory - both personally and for Juventus, a club that had been waiting for it for so many years," he told Corriere della Serra.
Van der Sar had no chance of stopping the missile Jugovic sent into the bottom corner.