Aye, take this for what it is:
My girlfriend and me have teams with pretty much the same average quality (usually within 0.5 of each other), but she has a very balanced team of 4/5 star players whereas I mostly had 6- and 3-star players. My cup draws are several qualities tougher, but I generally have an easier time with CL and League. It's the choices we made.
Though this season we actually had the same cup level (which can be seen in History) and similar opponents, which supports the idea that though it's based on first eleven players, there are certain tiers of cups; "level 34-38", or something like that. She was on the low end of the qualities, I was on the high end (concerning first 11). That was a tough cup for her and a relatively easy one for me.

The main problem I see for you is finding good players on the first few days! Let's hope for your sake you don't get stuck with 27-29 year old Scout players that are barely 6 stars. Or massive bidding wars on the transfer market in the "start of the season frenzy".