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@p1zZ4

To start the quest you must talk to him first and trigger the prompt where he will ask you to bring a Pidgey at level 5 or less. You must talk to him before you go and catch a new Pidgey for this step.

Once you have talked to him, you can try showing him a Pidgey that fulfills that requirement. Once he has approved it, you will be able to train it to 90+ and evolve it if needed to fight his Pidgeot for the next step of the quest.

 

I hope this has resolved your issue. If you fought his Pidgeot, you should be able to fight Gary in the Kanto Elite 4 building entrance.

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