Somewhere around the beggining of the Let's Go Hunting arc in DIU, Josuke brings up that he "still hasn't beat Jumbo Ozaki's golf game".
I got curious and found out that this must be:
Jumbo Ozaki no Hole in One Professional (1988) for the NES, Jumbo Ozaki Super Masters (1989) for Sega System 24 or Jumbo Ozaki no Hole In One (1991) for the SNES.In the Chili Pepper arc, Josuke can be seen with an SNES controller, and Part 4 taking place in 1999 makes it the most likely that he is playing Jumbo Ozaki no Hole In One.
But still, maybe he has some other systems lying around and can't beat "Hole in One Professional" even a decade later? Certainly isn't a professional.
To be honest tho, I am autistic for mostly JJBA and not videogame consoles, so I would appreciate uhhhhhhhhhh if anyone sent me an email to tell me if im wrong idk. But like, kindly.