Gary Neville found himself trying to combat the reigning Ballon d'Or recipient and the World Cup winning captain en route to Manchester United's treble success 24 years ago.
That 1999 triumph remains iconic - with the Red Devils still the only English side to ever complete the feat. Before their late, late show against Bayern Munich however they had to overcome Italian champions Juventus, the side who had made the previous three Champions League finals.
United would stop them making it four on the bounce, but the Old Lady pushed them all the way and provided such a test that Neville still purrs about the Bianconeri when quizzed now. Previously he'd declared them the best side he'd ever come up against.
He said: "Juventus were the benchmark We measured ourselves against them and I still look back on the team of Alessandro del Piero, Zinedine Zidane, Alen Boksic and Didier Deschamps as the best I ever faced. They had everything that I would love to have in my team."
Zidane had been the leading light for Les Blues as they won the World Cup just months earlier, Deschamps was the man lifting the trophy. Del Piero had scored 32 times in the previous season.
Juventus were in the midst of a dominant period, winning Serie A three times in the space of four years. They'd also completed a European double over the Red Devils in the 1996, securing 1-0 wins home and away.
Neville commented after those defeats: "Juventus were unbelievably good, so big and powerful as well as packed with talent. Just standing in the tunnel next to them was intimidating. I’d never faced such a formidable team." He went on to add: "It was the biggest battering I’ve ever had on a football pitch. They took us to school, boys against men."
Two years after that schooling however United were more of a match for the Italian side and held them to a 1-1 draw at Old Trafford. Ryan Giggs' stoppage time strike cancelled out Antonio Conte's early away goal and would leave the tie very much in the balance.
Back in Turin however Juventus appeared to have ended any hopes Sir Alex Ferguson and United had of claiming the European Cup. Filippo Inzaghi scored twice in the opening 11 minutes with the commentator that night saying: "Gary Neville was marking Inzaghi like the best Italian defenders, grabbing him. But Inzaghi still broke free and scored. He was the ultimate scabby poacher."
It would leave the Red Devils with a mountain to climb, but a challenge they would rise to.
Andy Cole said in the lead-up to the tie: "Juventus were the team to beat in Europe. We had played them before and never seemed to get the better of them." The English forward would end up scoring an 84th minute winner as United recovered to record an iconic 3-2 win.
The rescue mission was started by Roy Keane, who headed home after 25 minutes before picking the ball straight out of the net and running back to the centre circle. A yellow card for a later challenge would rule him out of any possible final appearance, but it didn't dampen his enthusiasm and determination.
Ferguson later said on his captain: “It was the most emphatic display of selflessness I have seen on a football field. Pounding over every blade of grass, competing as if he would rather die of exhaustion than lose, he inspired all around him. I felt it was an honour to be associated with such a player.”
Keane would go on to hoist the trophy aloft in the Nou Camp just weeks later, dressed in a suit. The Irishman played in 12 of the 13 games contested by United in Europe that season, yet commented that he didn't feel he deserved his medal at the time.