1.) Yes, because Ancelotti is just going to sit there and watch that happen for 90 minutes. You might be able to accomplish that in fits and starts, in patches, but it is unsustainable over 90 minutes.
2.) Those teams don't exist anymore, so what is the point of mentioning/referencing them?
3.) You are over-rating us. In 9 out of 10 encounters, we'd lose against Madrid. Heck, we might even play the perfect game and still lose. Madrid do possess flaws, but it isn't as if we are impeccable or indestructible. We have an ageing/slow defense, and our attempts at counter attacking have been pathetic and embarrassing thus far (we shall see how that changes this season, if at all).
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Mourinho is 51. Ancelotti is 55. Ancelotti started managing in 95, and Mourinho commenced with Benfica in 2000.