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So, how does Pickup Ability work? Does it work like the Drowsing Machine or does it just pick up random things as you walk?

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Pickup allows the player to receive free items. After a battle, any Pokémon on the team that has this Ability and is not already holding an item has a 10% chance of picking up an item, even if the Pokémon wasn't used in battle. It can be retrieved through the normal means of taking a held item.

So it does sort of pick up random items after battle, but the items differ every game and not all items are available through Pickup.

Here is a list of items and the percentage of getting them for every game.

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Thx, I was kinda confused.
The link was also very helpful : )
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The Pickup ability can be applied to a handful of Pokemon. Depending on the Pokemon's level there is a chance that a Pokemon with Pickup can 'pick up' an item.

The higher the Pokemon's level, the easier it is to get a rarer item. For example, in Black and White a Pokemon between Level 21 and Level 30 has a rare chance of getting a Rare Candy, but it's a common chance that it will pick up a Rare Candy if it is Level 91 to Level 100.

There is a 10% chance (1 in 10 chance) that your Pokemon will pick up an item after a battle, if it's not holding one already. Here are the items that can be obtained through Pickup. The percentages on the page aren't mathematically correct since they don't add up to 100%, so you can just substitute the percentages with stuff like 'Common', 'Uncommon', 'Rare' or whatever the heck you wish. xD

The Pokemon that can learn this helpful ability are Meowth, Aipom, Teddiursa, Phanpy, Zigzagoon, Linoone, Pachirisu, Munchlax, Ampibom and Lillipup.

Hope I helped. :)
Source: Above Link and Zis.

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10% chance pickup an item dose the odds double if the is more Pokémon with that ability?
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Pickup is an ability which has many good uses. You can get items which were discarded like an oran berry to a sitrus berry to even better ones. Outside battle you can get items. The items you get different at each level.

read more at http://bulbapedia.bulbagarden.net/wiki/Pickup_(Ability)

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