From what I have read, and from what other experienced posters have posted, apparently the troll engine takes the quality of your top 14 players for determining your cup draw.
I am not sure about many things in this game because the F******g devs and/or S******d management wont release any significant information on their game to confirm or deny what we have already theorized.
I started to save up my skill points a few seasons ago since I was put in bad cup draws vs stronger, higher level managers. Since I started saving, I have had easier cup draws. Maybe others have not had as favourable cup draws as myself, but I have still not won it but have come closer than before. I am now in the 1/4 finals for 2 of the past 3 seasons, so it does seem to have a better effect.
The drawback is that your players dont get better throughout the season, when they need it the most.
This is less of a vent than an informational post, but to make it a vent: Nordeus sucks in terms of their cup draw process....and many other things as well, but I am not wasting time venting about them here and now.