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TIL that if you plug a DualShock 4 controller into a Windows 98 machine, it just magically works and has analog support.

It also supports the Raphnet SNES-to-USB adapter. This was my original goal, and you can use Xpadder 5.6 (last W98 build?) to map it to keyboard controls. But if it's a two port adapter, it's a 50/50 shot which port it decides to latch on to.