Against a Sim AI you always can beat them regardless of prestige, but it'll cost you few HV and/or minutes guarantee. If you got time before signing starts, i'll start off with 2 HV, see where the battle stand and if you want to ensure more that you'll get him (in the case he is High/Very High considering the sim school) i'll keep throwing a HV till you demote the sim to Medium. If you have the luxury to spend CV then that'll be plan A