Paolo Maldini (36) vs Cristiano Ronaldo (20) Battle

36 year old Maldini vs 18 year old Cristiano Ronaldo. You d think that a 36 year old defender would have a hard time keeping up with a fast, powerful 18 year old attacker, let alone legendary player Cristiano Ronaldo. That was not the case as Maldini kept CR7 quiet for the most part. It s interesting to see how even a very young Ronaldo who loved to dribble did not dare to attempt dribbling too much on Maldini s wing. AC Milan vs Man Utd 2005, 2006.