Simply because Cup draw is based on starting quality of every team (actually for the best 14 players of the team).
so a team 2 levels above you, maybe has the same q with you (lets say 5* q team for you - 3* quality team for his lv) but when he starts buying his players for the new season, the 5* players of his lv, are 7* players for you.
Some things/methods you can do is
- sell all your good players before the last day, buy 14 3* players (or free agents), get an easy Cup draw and start building your team
- pump your 5* players to 8* players
- read this interesting thread

http://forum.topeleven.com/tutorials...xt-season.html