Several great points in this thread. Up until around 2002, we couldn’t compete financially with the Serie A and La Liga clubs. The Prem simply wasn’t generating as much money as it was today. I think Sir Alex himself once said that the priority for United every season is the league. This is, of course, a difference in mentality to Real Madrid that prioritises the Champions League.
Without meaning to be harsh to some of United’s loyal servants, the manager wasn’t ruthless enough in terms of getting rid of players who did not match the levels needed to compete in Europe. He kept on a lot of bang average players who didn’t go on to achieve much once he sold them on. Of course, their work ethic and commitment was crucial in the league, but on the big stage in Europe technical deficiencies were exposed very quickly.
A memory that sticks out in my head was Quinton Fortune in on goal one on one with Dida in 2005 and stumbling over himself for a toe poke that went wide.
Tactically we were deficient also. We stuck to very gung-ho flat 4-4-2. Get the ball wide, spam crosses and sustain the attacks. It could overpower teams in England, but in Europe?
Scholes-Keane as a midfield two lacked balance. Scholes had not yet become the deep-lying playmaker he eventually became and was still charging into the box at every opportunity. Keane also was more like a box-to-box destroyer and often departed his position. Better organised teams could play through us and were better at keeping the ball. See how Real Madrid eliminated us in 1999/00 by getting 3 early goals at OT.
The manager tried to tighten the ship with the Veron signing. It was a big feat for us to sign a world-class player from Serie A for that big of a fee. While it did not work out, we switched to a 4-5-1 in Europe. The only issue was that, by now, we were in a transitional phase. Our experienced core of players were entering their 30s (Neville, Butt, Scholes, Giggs, Ruud) while Rooney and Ronaldo were still kids.
2006-2011 - we were genuinely one of the best teams in Europe.
We should have won in 2007, but Kaka was just too good and the only players with experience of the latter stages of Europe were in their 30s. Regardless of our defence being decimated by injuries, we must remember that in 2006-07 we had just gone three years without a league title. It was still Cristiano’s first world class season. We were simply not ready to win the Champions League.
2008 - We dealt with all the previous obstacles holding us back. We spent well in buying Nani, Hargreaves, Anderson and Tevez. We were tactically astute. We were truly the best team in Europe. The fact that Park and Saha didn’t even make the bench in Moscow spoke volumes about how strong our squad was.
2009 - We came up against maybe the greatest club side of all time. We could have put 15 players out there and Barca would still have schooled us. Fletch and Hargreaves were a big miss, sure. But that triangle of Messi, Xavi and Iniesta? You can’t defend against it.
2010 - The manner of our exit was annoying but even had we beaten Bayern, and then the French team they faced in the semis, I’m sure Inter or Barca would have beaten us in the final. We were in the “there’s no value for money” era at this time. The fact we replaced prime Cristiano and Tevez with Wigan’s winger, Obertan and finished Michael Owen spoke volumes. Chelsea did the double over us that season too. We weren’t even the best team in England, let alone Europe. Despite being tactically astute, our player quality was not befitting of a club of United’s stature. I think Sir Alex overachieved here. We were carried by workhorses in Fletch and Rooney. Carrick had an off-season. Our creativity was still heavy reliant on Scholes and Giggs who were into their 30s. The fact that Gibson got so many games spoke volumes. I don’t want to be harsh but Nani and Valencia were not exactly Champions League winning level wingers either.
2011 - We had a fortunate run to the final and Barca were once again just a class above. Once again, I think Sir Alex overachieved given how weak our squad was in comparison to other top clubs in Europe. To think that we started Fabio and Chicharito in a Champions League final!
2012 - Sir Alex showed faith in his squad players in the group stages and we paid the price.
2013 - while we faced injustice against Real Madrid, I think our aging squad, even had it progressed, would not have been able to handle Bayern and Dortmund’s gegenpressing. In a way, we had become like the Italian teams of the past and it was a total reverse of our problem of the 90s. We were tactically astute and could play on the counter well, but physically we weren’t up to scratch. We were still reliant on Giggs and Rooney had lost a yard of pace too. Kagawa was a tidy player but lacked pace and strength. We relied heavily on RvP, who himself had a habit of bottling big chances from time to time.