For this Achievement you have to win a match with every single superstar, diva and legend on the roster to be able to get the legend's you have to unlock them throughout season mode so i would recommend doing this first.
I would also say change all of the sliders in your favour by going in to the settings and you will want to change the difficulty to hard so that you can win every match with every superstar and also fight against every superstar of the roster to unlock two achievements in one people are finding this can glitch and I have typed up a list on google spreadsheet that anybody can access and print out to keep a check of.
for the last match 68 you have to change difficulty from hard to legend then play as triple h vs candice for some reason otherwise both cheevies wont pop. (this will not unlock the legend difficulty you have to do a separate playthrough for that I've done the list to get 2 achievements in 1 playthrough otherwise you have to playthrough 3 times just trying to save people time).
here is the link : https://docs.google.com/spreadsheet/ccc?key=0AtFfYJRRdpFwdDl...