99-05 why didn't we win the champions league again?

Yeah, that's how I remember the away game as well.

We played well in the second leg, but really gave it away after Keane's own goal.
If VAR were around we’d have had a pen at 0-1

didn’t Ivan Campo palm the ball over the bar in front of K stand from a Cole or Yorke header?
 
I remember we beat West Ham 7-0 at OT the weekend before, and the Spanish press were writing off Real’s chances. Then Redondo happened…
7-1

we went 1-0 down didn’t we.
 
2001 we brought in Veron but I can’t help but wonder if we could have really got Vieira when the link surfaced. Keane, Vieira and Scholes would have been dynamite away from home.

Or Davids who still had it in the tank in 2001 for about 3 more years. Later revitalized Barca for a half-season there, around 2004 think it was.
 
I still think despite that treble success that English football still lagged behind the Spanish, Italian and even German football back then.

I think it was just luck of the draw in certain circumstances where we drew an eventual finalist early on in the knockout stages or we get knocked out on away goals when we shouldn’t have been.

I still believe we should have knocked out Porto in 03/04 and Leverkusen in 01/02, especially the latter where very poor finishing cost us.
 
Compare the talentpool of UK, Ireland and Nordic countries...with Germany, Italy, Spain, Portugal and South america.
Queiroz gave us access to C.Ronaldo, but even then we couldn't keep him.

We had a lot of mediocre players, but they gave it their all for Fergie. Even then it wasn't enough most of the time.
 
Too obvious to say “because it’s a cup competition so Lady Luck has an outsized influence”?

The Scholes offside goal against Porto. The Nani red card against Real. Moments like that determine your fate, they don’t in the league. The best team in Europe wins the champions league maybe one in every three years? All you can ask is to be good enough that teams on the continent are saying “oh f**k, we’ve got Man Utd” if drawn against us.
 
Replace Schmeichel properly and buy some good central defenders and I'm sure we'd have at least won another CL in that time. Sir Alex should've also looked sooner for some different perspectives in regards on how to deal with European football. Sometimes a more conservative approach would've gotten us further, instead of going gung-ho every time. A little bit more luck would've helped as well.
 
Why didn't you include 06 and 07?
I feel that was a different team. We really hit a low point in 05-06 not even getting out of the group stage, Keane had left months earlier, Ruud was clearly wanting to leave and we were just about to buy Evra and Vidic as the squad needed some work. 06-07 was the start of the next great Sir Alex side.
 
I would say a bit of naivety from SAF in Europe.

He was a fantastic manager in the PL as his 'go for the jugular' style worked well over 38 games but pre-Quieroz (when we became more aware, solid and flexibile) we shot ourselves in the foot too often in one-off games where grinding out a result was needed - Porto and Leverkusen spring to mind.