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I have fought him multiple times after completing the Massive Mass Outbreak storyline and the Volo storyline. How do I unlock his harder rematches?

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so at the place with the fighting lady? (i forgot what it is called )
It unlocked somehow. I would still like to know how.
Yes, at the training grounds.
You should comment instead of answering if you're not sure your answer is correct.
I'm not SURE if this is how I eventually did it, but it might be...

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His tougher team is unlocked after you complete Mission 27 (obtain every Pokemon and play the Azure Flute to Arceus). His Alpha team is unlocked after you defeat his tougher team.

Ingo (Bulbapedia)

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