PokéBase - Pokémon Q&A
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People say you can’t transfer items between generations. I remember something about items transferring between Gen 1 and 2 (even tho gen 1 had no items).

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You can't transfer items between gen 1 and 2 because Pokémon cannot hold items in gen 1. However, while you do get items when you trade a Pokémon from Gen 1 to 2, these items are generated in the Gen 2 game and cannot be sent to gen 1. :P
Oh so that’s probably what my friend was talking about @Staka~
And why does this question have 1 downvote I have no idea.
It is possible to transfer items between Gens 3 and 4, but that’s the only one I’m aware of. Pokébank and Gen 5’s transfer systems will move items back to the Gen 4 game’s bag. I’m not familiar with the transfer system between Gens 1 and. 2, though.
So it is possible at least.
I have heard that you can transfer held items from Generation 2 to Generation 1. The item will be completely hidden while the Pokemon is in the Generation 1 game, but it'll remain intact if you transfer it back to Generation 2.

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In the case of Generation 1 to Generation 2, you cannot transfer items from your bag to Generation 2, but the Pokemon you obtain may hold an item when transferred. The item you get from transferring is dependent on the Pokemon's catch rate for that game. This page on Bulbapedia shows a list of Pokemon by their held item in Generation 2. The items are generated in Generation 2, and sending held items back to Generation 1 is impossible.

In Generation 4, Pal Park allowed held items to be transferred on Pokemon from Generation 3. Just about every held item can be transferred, except for mail (the Pokemon won't be allowed to be transferred) and the e-Reader berries (which will become Enigma Berries).

Every other generation has your items returned to your bag. Poke Transporter doesn't include any held items on Generation 1 Pokemon (probably since a handful were Gen 2 exclusive, such as the Brick Piece), and held items on Generation 2 Pokemon get sent back to the bag when transferred.

So, in general, no, you can't directly transfer items except from Generation 3 to Generation 4, though you can potentially influence it in Generation 2 by capturing certain Pokemon. In every other generation, it's impossible.

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So it is possible to transfer items from one to another generation. It’s just that people obviously don’t know this.
I don't blame you, transferring items from 3-4 legitimately caught me by surprise when I was looking up verifiable facts for this answer.