Wipeout XL was released in 1996, but according to Wikipedia it worked with the Namco NegCon.
That controller was made for Ridge Racer and released when the PS1 was launched.
So the first question is, does the emulated version support analog input?
I've no idea if the emulated version supports analog, but I
can vouch for Wipeout XL working with an analog NegCon.
Grabbing one of those controllers years and years ago was one of my choice flea market picks. I'd used a NegCon back in the mid/late-90s at work, and it was an
awesome controller to play Wipeout XL with. Heck... even after all the years, XL is by far my fave Wipeout release. Fury was a gorgeous visual update, but XL is still my fave.
Hmm... now I'm wanting to go break out my PS-to-USB convertor and plug my NegCon in and try it all out...