A lot has changed in the 15 years since Manchester United and Juventus last met. The two clubs, who combined have lifted the European Cup five times, have not played each other since February 2003, when the Champions League still had two separate group stages.

United won both matches; 2-1 at Old Trafford and 3-0, rather remarkably, at the Stadio delle Alpi.

There were electric European nights in the 90s, too, nights of memorably high drama, when dreams were shattered and legends were made. In the 1999 semi-final second leg in Turin, Roy Keane produced a captain’s performance of rare genius, leading Sir Alex Ferguson’s Treble-chasing side to a final he knew he wouldn’t be a part of.

Eighteen months prior, United edged Italian football’s Old Lady 3-2 in a pulsating encounter in front of an enraptured Old Trafford crowd.

In 1996, Marcello Lippi’s Juve – en route to the final – beat United home and away in the group stage, two games which formed the basis of a tremendous mutual respect between the cigar-chomping Italian and Ferguson.

They were nights that entranced Europe. They were nights of Zidane, Del Piero, Scholes, Beckham, Trezeguet and Thuram.

They were also nights on which United, with unfailing certainty, advanced to the next stage.

Now, with the balance of power in English football having shifted to the other side of Manchester, United will approach their return to Turin with as much trepidation as enthusiasm.

Since that productive trip to Piedmont 15 years ago, a lot has changed. Having reached three Champions League finals in four seasons between 2008 and 2011, United have struggled to maintain their eminence on the European stage, with Ferguson’s retirement in 2013 triggering the club’s most difficult chapter since the turbulent nascent days of the Scot’s 27-year reign.

Juventus, meanwhile, spent time in the wilderness following the Calciopoli match-fixing scandal that rocked Italian football. The Old Lady were banished to the second-tier and stripped of their 2005 and 2006 Scudetti.

But, while United have tried and failed to find a worthy, long-term successor to Ferguson, Juventus have emerged from their ignominy and shame to re-establish command of Serie A.

United’s Premier League record since Fergie’s retirement reads: 7th, 4th, 5th, 6th and 2nd. They have spent time out of the Champions League – time which has admittedly yielded a trophy in the Europa League – and their diminishing stock on the continent is best summed up by their failure to qualify from the group stage in 2015 under Louis van Gaal and the shock last-16 exit to Sevilla last season.

Juventus’ experience on the domestic front could not be in starker contrast. The Bianconeri are hunting for their eighth successive title this season, having tasted Serie A success in each of Massimiliano Allegri’s four seasons at the helm.

The 51-year-old’s reward: Cristiano Ronaldo. Yes, Juventus issued the most significant statement in the transfer market this summer, splashing out £100million to acquire the Portuguese superstar’s services.

Ronaldo, of course, was pivotal to United’s Champions League triumph in 2008 but will be plotting their downfall now, a decade on, similar to when he destroyed Ferguson’s dream of one final European trophy in 2013, scoring on his return to Old Trafford as José Mourinho’s Real Madrid sent United packing.

The rationale behind Ronaldo’s move to Italy was simple: Juve want to take Madrid’s European crown. Three months ago, the idea of anyone dethroning Real was faintly ludicrous but Juventus, having lured their prized asset away from the Spanish capital, Allegri’s side are thinking big.

United – although Mourinho will never admit it – are just thinking of staying in it. Thursday’s draw handed United a difficult group, with Valencia and Young Boys completing the quartet.

As Allegri plots European dominance, Mourinho seems to be fighting a losing battle at Old Trafford. The 55-year-old has delivered two trophies and a second-place finish in his two years in charge, but those accomplishments have been largely overshadowed by reports of behind-the-scenes friction.

Many of those reports have centred on Paul Pogba, United’s star Frenchman with whom the Portuguese shares a fractious, tabloid headline-dominating relationship.

Mourinho’s immediate concern is generating some positive publicity. After a wretched start to the Premier League campaign that has included dismal defeats to Brighton and Hove Albion and Tottenham Hotspur, the United boss must view the Champions League as a platform on which to regain a sense of stature.

Liverpool‘s run to last season’s final while finishing fourth in the Premier League will surely give Mourinho hope. But for United to thrive in Europe, they need to exercise more ambition and courage than in their whimpering two-legged display against Sevilla last time out, when a team with a goal difference of minus six in La Liga defied the odds and deservedly advanced to the quarter-final.

Ronaldo’s return to Old Trafford, Pogba’s reunion with Juve, Mourinho’s quest to remain relevant; United and Juve will be box-office stuff once again. However, they will be two games played out against a dramatically different backdrop, one which has a Ronaldo-led Juve gunning for glory and United already scrambling to salvage their season.