DosboxX or PCEmu will often play stuff that requires Win98 or before.
For things that run on XP, I would recommend VMWare ESXi with your graphics card running through PCI passthrough. It doesn't handle 100% of all games (I've seen one or two that detect that combo as "cheating"), but it handles a lot.
My primary gaming rig runs ESXi with a bunch of VMs set up with various operatiing systems, and my graphics card is just old enough that I can find an old XP NVIDIA driver for a different card of the same architecture that works with it.
DosboxX or PCEmu will often play stuff that requires Win98 or before.
For things that run on XP, I would recommend VMWare ESXi with your graphics card running through PCI passthrough. It doesn't handle 100% of all games (I've seen one or two that detect that combo as "cheating"), but it handles a lot.
My primary gaming rig runs ESXi with a bunch of VMs set up with various operatiing systems, and my graphics card is just old enough that I can find an old XP NVIDIA driver for a different card of the same architecture that works with it.