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If two gym trainer challengers, or two gym leaders, face against each other, and neither type has any advantage over the other, who wins? Is it random?

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The winner of the Champion's cup rematch brackets are always random. However, if one of the trainers has a type advantage against the other it does have a higher chance of winning.

The same thing happened with the PWT in Black 2 and White 2. The announcer would have different dialogue if the win was an "upset" because of type advantages.

Source: Experience. I did the rematch bracket a lot after I beat the game.

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