PokéBase - Pokémon Q&A
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Every time you defeat a new trainer stage, you receive a jewel. Will I be able to chain for jewels by defeating that stage over and over again?

I'll test this and check back soon.

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To put it simply.. no.

You only receive a gem the first time you battle a trainer.

Source: I just tested it twice

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I cant be evil anymore...oh well thanks anyways!