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Gym Leaders and important characters will always win against unimportant NPCs.

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It is sorted, so that you will vs Gym Leaders/Characters that are imporant For example Bianca in the second and final round. In the first it is randomized. the gym leaders/Important characters will always win against non-important characters.
Source: Experience

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The Gym Leaders will always win against the trainers that are not important, such as Youngsters and the like. However, if there is no Gym Leader in a battle, then the winner is usually the Veterans or Ace Trainers.

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