Three minutes was what separated Manchester United from a fairly routine win over Valencia back in February of 2001.
That would have been enough to secure their passage into the quarter finals of the Champions League back when the competition had a second group stage. Wes Brown’s late own goal, sliding into Fabian Barthez’s net from a Vicente cross, denied them that, though.
In truth, that was the only reason to remember what was an unremarkable match. Drawn alongside Sturm Graz, Panathinaikos, as well as Valencia, United were always likely to make the final eight.
But these dropped points ultimately saw Valencia finish ahead of Sir Alex Ferguson’s side, giving them the superior ranking for the quarters. Man Utd were paired with Bayern Munich, who they eventually lost to, while Valencia progressed past Arsenal.
Valencia, then under the stewardship of Hector Cuper, went on to make the final of the Champions League that season, ultimately losing out to United’s conquerors Bayern Munich. This sequence was reflective of a great period of European underachievement for Ferguson and his players at an otherwise glorious time for the club.
Ferguson’s Man Utd were never more dominant domestically than they were between 1999 and 2001, when they won three straight Premier League titles. In the 1999/2000 season, they finished top of the pile by a massive 18 points. The following season, they finished top by a not so massive, but still substantial, 10 points.
This dominance never truly translated into continental prowess, though. Every United fan remembers that night at the Camp Nou, when two stoppage time goals gave them their first European Cup since the days of the Busby Babes in the 1960s.
Everything about that night, from Clive Tyldesley’s commentary to the sight of Lothar Matthaus slumped on the Bayern Munich bench, is written into Man Utd folklore, but those sort of scenes should have been witnessed more often over that time period.
United’s strength around the turn of the millennium and the years that followed was obvious. They boasted arguably the best centre back in the game at the time, Jaap Stam, and two of the best central midfielders, Roy Keane and Paul Scholes.
They had Ryan Giggs on the left and David Beckham on the right. Up front were Andy Cole and Dwight Yorke, a pairing that is still referenced to this day as one of the most effective goalscoring duos ever seen. In 2001 they also signed Ruud Van Nistelrooy, a pure goalscorer of which the kind are exceptionally rare.
And yet over this spell, United only made one Champions League final, in 1999 when they won it. Valencia, in contrast, made two finals, only underlining how inconsistent Ferguson’s team was at the peak of its powers. Ferguson has admitted himself that United should have made more of an impression over this period, with Valencia’s return to Old Trafford in the Champions League this week throwing the mind back to such a time.
But the point can be expanded further. Manchester United might be, by some measures, the biggest football club on the planet, but they are also the biggest Champions League underachievers going. That is something that still hangs over the club, even to this day as they embark on another campaign.
Over their entire history, which by the measure of most has been glittering, Man Utd have only ever been European champions three times - in 1968, 1999 and 2008. That leaves them ranked below almost every elite counterpart with the exception of Juventus, who only have two European Cups to their name.
Ajax, for comparison, have been European champions four times. AC Milan and Bayern Munich have won it five times, as have, most damningly, rivals Liverpool. On top of this, Liverpool have made the final of the Champions League three times since 2005, winning it once. That puts them on level pegging with Manchester United who, over that period, have been a far stronger side, on the whole.
United see themselves, at least in terms of size and stature, on a footing with the likes of Barcelona and Real Madrid - record annual revenues of £590m were announced just last week - but there is an almighty gulf between the Old Trafford outfit and the company they claim to be a part of. That may not be such a standout statement in the current climate given the troubles presently being experienced by Mourinho and his team, but this is something that predates the Portuguese. This is one thing he cannot be blamed for.
Some excuses have been made. In the 1990s, Ferguson could get away with claiming his players were still growing accustomed to European competition. The years since the Scot’s retirement have been barren, with United locked out of the Champions League for three of the six years since 2012/13. But as a club that has won more English top flight titles than any other, there is a clear fault in their continental record.
No time period demonstrates this better than the years that straddled the turn of the millennium, when Valencia last came away with a result from Old Trafford. Ferguson would likely look back at the period between 2008 and 2011 as his golden age in European competition.
United made the final of the Champions League three times in four seasons over this period, winning the competition in 2008. But Man Utd were at their most dominant as a side in the years that followed Ferguson’s first Champions League triumph in 1999.
Mourinho has too much on his mind to think about addressing this imbalance right now. Man Utd have enough of a challenge just qualifying for the Champions League this season never mind winning it. But with Valencia once again in town memories are recalled of a time when the Old Trafford club could, and should, have been European champions more times than they were.
Ferguson once said that Manchester United were “the most romantic club in the history of world football.” That might be true, but this has counted for very little when it comes to Europe.