They really drove home the 'underdog' aspect, but that was quite literally the only possible method of victory. The copy is controlled by a computer that is incapable of miscalculating and can calculate several orders of magnitude faster than any human being. Not even with ten thousand years of training would it be possible to truly equal its level of control and technique. At best, you could rival it, but it is impossible to ever surpass it in that aspect. A machine will always have better focus, better control, better judgement, and never make unnecessary movements. The only way to win is to introduce something it can't copy: random chance. Also, MC should've unequipped everything and emptied his inventory so they both only had the flail, then it wouldn't have been able to put up a fight at one hp. I think this was definitely intriguing, but probably the most ridiculous challenge, yet for Greed. For Kraugel, I'm not sure it's possible to overcome such an insurmountable gap since he can't get better equipment or level up for the trial. The only way I can think of is to lose to something else more, whether by accident or design.