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There seems to be a way to connect a controller to the PSP through its USB port, like shown in the picture below of a "DOSO PSW-303".

Is there a way to do something similar that works with any generic USB controller?

enter image description here

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    That device seems to use customized PSP firmware and customized hardware, so probably not unless you create your own customized firmware and hardware.
    – user86571
    Commented Jun 7, 2019 at 16:00

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From my findings, connecting a generic USB controller to a PSP through its USB port requires a master intermediary device, since the PSP can only function as a slave USB device, as shown below:

(Block diagram: (original slave device) -> (intermediary master device) -> (generic USB game controller)

The intermediary device in question can either be a USB-compatible microcontroller (link #1, 2008, "gr8npwrfl"), or a PC (link #2, 2010, "ThirdSeason").

The PSP also must be loaded with custom firmware for such an idea to work.

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