To get both Ahead of the Pack and And STILL Champion... the easiest way would be to set up either a 10 or a 20 minute Scramble Match on Legendary difficulty as a Defending Champion. Unless you are really really good, I would suggest doing it on the 20 minutes. Doing it on 5 minutes, means every minute, another superstar would come out, and will usually interrupt your pin. On a 10 minute match, every 2 minutes one will come out. With a 20 minute match, every 5 minutes. Your best bet would be to go out first and get a decision in the first 5 minutes, when there is noone else involved. Then just make sure noone else wins for the next 15. Also you do need a decision. If NOONE gets a pin or submission, the match ends in a draw.
Several people prefer to make 4 CAW's, and leave their stats untouched. (Their overall would be 40), and pick a good superstar. Start at #1, put one of the CAW's against your powerful superstar and beat him into a pin/submission, and just wait out the last 4 minutes.