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Champions League: Alex Ferguson faces the 'acid test' of latest Manchester United generation

He rebuilds his teams in cycles but is his latest creation ready to win the greatest prize again? They must first get past Real Madrid

There was a moment when Sir Alex Ferguson mentioned the number of European Cups that Real Madrid have won and, pausing for a moment to marvel at that record of nine titles, conceded it was one benchmark he would have to accept was beyond him.

t made you wonder whether, 30 years since his Aberdeen team beat Real Madrid in Gothenburg to win the European Cup-Winners' Cup, Ferguson should not have more than the four European trophies in his career – two of them Champions League titles. Harsh? Perhaps, but when you consider his dominance of English football it is reasonable to expect Manchester United might have won more.

First things first: this is one of those occasions in European football, that has a resonance that goes far beyond Uefa's rehashing of the great competition and its new incarnation as a global television giant played out by multi-millionaires in neon boots. No matter how modern these two great sporting and commercial behemoths can feel at times, this is a game that speaks of the history of European football.

Yet for United, as Ferguson acknowledged yesterday, it is also a kind of beginning for the younger members of his team. "The acid test is [tonight's game]," Ferguson said. "I have no doubts in my mind about that." The cycle of a new United team, with some familiar old faces sprinkled in, is beginning again and tonight is one of those games when good young players are measured for their suitability to be part of United's future. The last 10 years of United's Champions League history, since they last played – and lost to – Real Madrid in the quarter-finals in 2003, can be broken down into distinct phases. There was the initial underachieving as the team that Ferguson built at the start of the last decade was gradually broken up. There were early exits in 2004 and 2005 to Porto and Milan, then the disastrous failure to make it out the group stages in the 2005-2006 season shortly after Roy Keane's infamous MUTV interview and his subsequent departure.

Within two seasons of that embarrassment, United had won the Champions League for a second time under Ferguson in 2008, having been eliminated by Milan in the semi-final in 2007. That ushered in a golden era of three finals in four years between 2008 and 2011, with the quarter-final defeat to Bayern Munich in 2010, the only time in that period they failed to make it to the final.

Then last year, came another reality check, similar to that one experienced in the 2005-06 season, when United failed to make it out the group stages again. The rebuilding continues and the generation of Tom Cleverley, Danny Welbeck, Phil Jones, Chris Smalling, David De Gea, Rafael Da Silva and the newly arrived, albeit vastly experienced, Robin van Persie are asked to show whether they can take United back up to being contenders again.

"They have great spirit about them," Ferguson said. "I know people say we are not as good as Manchester United teams in the past, but sometimes we get foggy recollection about the past. I do myself. The reality is that this team doesn't know when it's beaten, which is a good quality to have. We have some good individual players.

"I think we are a wee bit different in that we build teams to last a while, with youngsters in the squad, that gives you a longevity and consistency to your challenge. Not necessarily giving you the trophies that you want to win but it gives you the chance to be there. Eventually that young squad will work together and mature together and you create a team that can win the Champions League again."

Ferguson's successful sides in Europe have tended to get the better of an opponent over a couple of seasons. For the 1999 Champions League winning side it was Juventus who were the benchmark. Beaten by them in 1997, United came back two years later to win that epic semi-final.

The United team that won the Champions League in 2008 had twice previously been eliminated in 2004 and 2007 by the great Milan side led by Kaka. But United evolved and by the time they played Milan, albeit by then without Kaka, in the last 16 in 2010, United won 4-0 in the San Siro and 7-2 on aggregate.

Now Ferguson is trying to build again. That is not to say there are not players of great experience in his side, indeed six of those who started in the 3-0 defeat to Milan in the semi-final away leg in 2007 are still at the club. But nevertheless, after last season's failures it feels like a distinct new era, potentially Ferguson's last.

Cristiano Ronaldo's presence will be a reminder of who United have built in the past. He was the key player in the seasons after Keane and then Ruud van Nistelrooy left, although United still reached the 2011 final after he too had left. As ever with United, the key players are never replaced like-for-like, rather different characters step to the fore.

There was much hand-wringing over finding a "new" Keane, until Wayne Rooney and Ronaldo emerged. So too, Van Persie has filled a void not occupied since Ronaldo's departure, although they are clearly very different players. The likes of Jones, Welbeck, Smalling and Cleverley are following a path well-trodden by United's best young players. Eliminate Real Madrid and suddenly the picture changes and expectations rise.

Should United eliminate Madrid, thoughts begin to turn to Barcelona and the ultimate test. United beat Barcelona in the semi-finals in 2008 but since then Barça's development has eclipsed their own. Had those two finals United have lost to Barça gone the other way, then Ferguson would be the most successful manager in the history of European football.

As things stand, knocking Barcelona off their perch looks rather more than daunting. At times, it feels damn near impossible. But these things have a habit of going in cycles, and empires in football fall rapidly. Real Madrid waited 32 years between their sixth and seventh European Cup wins, longer than United's 27-year wait for a league title post-Matt Busby. Ferguson has always pursued a swift renewal of his teams, and for his younger generation, this is a crucial step.