I worked out a cheat for really easy win:
start a new GM Mode, when it say you have to pick between WWE Roster, and Draft Roster, press Square, and it should up with a screen with a list wrestlers, turn off all the wrestler that are not on the RAW roster(This Includes all the free agents as well, as Smackdown!), then continue, and select WWE Roster, then pick RAW, now you should be able to just have 1, or 2 matches a week, and win.
IMPORTANT:..........DO NOT FORGET TO RENEW CONTRACTS WHEN NEEDED.
PS: Personally, I will not be going this way, because I want to do it the hard way!
Update:
You have to have at least 25 superstars active, so keep 5 of smackdowns least popular superstars.(Maybe some divas as those 5 superstars.)
So you will have to try a tiny bit each week(I mean a "Tiny" bit)