PokéBase - Pokémon Q&A
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So, for example, Entei is encountered and a Togekiss uses Yawn on it. Entei flees, but is encountered later. Will Entei still be drowsy and fall asleep, or will it not be drowsy anymore?

I doubt that roaming Pokemon do keep their drowsiness after they flee and are encountered again, but I just wanted to make sure before I find a Pokemon with a move that causes sleep on the first turn that it's used.

Any specific gens?
An answer for Gen 4 is more important to me right now, but, if possible, an answer for all Gens would be appreciated.

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If the roaming Pokémon is damaged or afflicted by a non-volatile status condition, it will retain this when it is next encountered.

Drowziness is volatile.

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