I get the feelin that thats the top of his server, the engine wouldnt put together players with 20Q difference between each other if it wasnt.. but idk
Usually cup draws work like that:
Engine calculates the Quality of your best 14players and makes the draws..

3*(2*after promotion) team = you'll be the highest level of your cup
4*(3*after promotion) team = 1Level higher than you
5*(4*after promotion) team= 2Levels higher than you
6*(5*after promotion) team = 3Lvs
etc..
If you have 25.05-29.94 Average Quality of your best 14 players as level 1, thats 6Stars, next season you'll be Level 2 with 5* team and your cup will be Level 5.
2+3lvls higer(cause of 6* team)=Lv 5 cup.
In that Lv 5 cup you'll find Level Lv 5 managers with 2stars team
Lv 4 teams with 3stars team
Lv 3 with 4stars teams
Lv 2 with 5stars team
You could find some Lv 1teams that have 6stars and didnt promote last season aswell.