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Ash entered the Sinnoh region with Pikachu and Aipom, Team Rocket arrived and took Pikachu away, but their hot air balloon went down and Pikachu flew into the middle of a forest, which is where Dawn met Pikachu and tried to catch him. Ash was determined to find Pikachu , and he found a Starly and caught it so it could search from the sky.

So practically, Starly was his first in Sinnoh region.

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