PokéBase - Pokémon Q&A
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Is there any way to send ANY kind of item from 4th gen to 5th gen (I know TM's/HM's can't, but berries, hold items like damp rock?)

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No. Source: Personal experience.

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I can vouch for that as well... Gamefreak...
that blows. all those heart scales, amongst things, from my pokewalker are a waste of time for gen V then