To easily win the Royal Rumble in Season mode, simply skip the match to cut to a scene of your wrestler celebrating the win. You will still get the money for winning the match. Also, to easily win the SmackDown! Royal Rumble in Season mode, you can just simply skip it as well. After you skip it, Kurt Angle usually will win, but after he wins Vince McMahon walks out and says that Kurt cheated and he will be disqualified. You will then only have to fight the last five people instead of waiting for all thirty to come out. If you defeat the last five people, then Season mode will continue as if you won the entire thirty man rumble.