PokéBase - Pokémon Q&A
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I was on bulbapedia derping around, and I saw the catch rate page which got me thinking about the 255 catch rate. So I go on White 2 and start trying to catch stuff with pokeballs, and I automatically catch a woobat, roggenrola, and watchog with full health. And they all have catch rates of 255. Is this a coincidence or what?

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No. 255 means that they're easy to catch, its not always a catch.

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what is the percent chance?
For a simple percentage, a Pokemon with 255 catch rate will have a 33.3% chance to be caught with a regular Pokeball with full HP and no status problem. So if you use an Ultra Bsll or something, you can tell it's going to be easy to catch.
Because the catch rate is 2x Higher