I have Master of Orion 2, which came out when DirectX was in version 1.0. It technically executes in Windows 10, but the graphics are glitchy.
When they re-released it on Steam along with the MoO remake, they actually packaged the DOS version with DOSBox rather than release the Windows version.
I think this is largely only true with Windows games from the '90s using still-nascent 3D apis. Many of these games were broken on modern versions of Windows by the time Vista came out.
Once you get to the early '00s, you can still find a lot of games that are broken, but the culprit is usually changes in hardware and driver behavior rather than Windows itself.
No, not really. Even if you ignore DRM which practically makes ALL games from the XP-Vista era unplayable (which I ignore since that is often not better in Wine), just search around for the amount of workarounds that are required even when you apply these patches.
I wasn't saying that fewer games from the '00s require fixes, I said that the things that are broken in them are more often caused by factors other than Windows itself. The most common compatibility issues I see with games from this era are caused by changes made to GPUs and/or their accompanying drivers.
Take for example the first two Splinter Cell games. Certain shadows on them do not render on modern GPUs. The root cause isn't any changes Microsoft made to DirectX or Windows, but Nvidia deprecating a feature they relied on in their GPUs and their drivers not providing any kind of fallback. If you play these games on Windows XP with hardware from 2003, they run fine. But if you play them on Windows XP with hardware from 2007, they do not.
Wine fixes a lot of these games because it is already providing its own translation layer for graphics calls, and any GPU vendor-specific DirectX stuff gets translated into hardware-agnostic Vulkan. These same games are often easy to fix on Windows using DXVK (Wine's DirectX translation layer), or wrappers designed for late '90s and '00s games like dgvoodoo2.
The big elephant in the room is DRM, with popular solutions like StarForce being deliberately broken by Microsoft.
