The best feeling in this game is when one crashes the semi's/finals of a higher level cup. It's a difficult task, but not impossible. Most those managers two levels above you, aren't real active and often aren't highly skilled, so with the correct role of the dice, a deep run is still possible.
I'm facing a level 27 in the first round (I'm level 24), so the level gap is present; but his players are all 2* for his level, so I know he isn't highly active and being opening day, I doubt he'll be winning any bidding wars.