I have had good success with Wine on a Linux machine in the past. Usually works better for Win95 programs than all 'compatibility' modes on Windows proper.

So you might set up a Linux system in parallel to your Win 8 on your computer to run old Windows software. Sounds strange, but it works.

But unless I'm wrong Hyper-V does not support Win9x guest so it's is useless for OP.

Funnily, I was just rearranging some of my old CD-ROM games yesterday, among them Fade to Black.

For some reason, I recall being somewhat bored when I played the game a long time ago. I finished it though, so there must have been something good in it. But at least I never got an urge to replay it. I have much more fond memories of e.g. Another World (Fade to Black was like the third game in that series, at least a spiritual successor, right?). Does that really work nowadays, including 3D acceleration for early Direct3D games etc.?

The last time I tried running Win98SE in VMWare Player was a big letdown. At best I got it running like it had only basic SVGA graphics (640x480 with 8bit colors or something like that), which meant it was useless for Direct3D games. I'm unsure if I even got the audio to work.

When I googled for it back then, it seemed the VMWare developers weren't simply interested in developing Win9x support, especially for gaming purposes. Apparently their main market is for people to run many modern OSes side by side (Linuxes, WinXP-Win8 etc.).

Then again, installing 32bit WinXP into VMWare Player probably allows you to install and run many early Win9x games that don't run on 64bit Win7/8 due to e.g. 16bit installers or code.

That's the most foolproof method that I've also used, even though I prefer running the old games on my more modern PCs. For one the old hardware will also die at some point, and also old cranky desktops taking precious room is a problem for me.

Fortunately I was able to make an old IBM ThinkPad T41 laptop (running Win98SE) run great with early Win9x/Direct3D games. It is pretty much perfect for that purpose and takes little room too. You can still find Win9x drivers for it at the IBM site.

Also it must be remembered that quite often the problem with old Windows games is not the OS itself, but the hardware and their drivers. Some games don't like multicore CPUs or too high CPU speeds (Interstate'76 anyone?), or modern graphics cards or drivers don't support some legacy features of old hardware (like the z-buffer problems in Heavy Gear 2; albeit I think there was some workaround for that) etc.

So it has Direct3D HW acceleration? Maybe I'll try it again.

Yes, Virtualbox has Direct3D acceleration for Win98, but unfortunately you have to disable CPU acceleration or Win98 won't work. VMware has full GPU and CPU acceleration in Win95-ME.

P.s., Timppu, I don't suppose your avatar is from Cobra Mission? I loved that game!

Someone finally recognized the game! :)

They have recently upgraded the virtual graphics card. Seems to work well on the games I've tried. Not saying it's 100% guaranteed. Just worth a try.

You could probably find an ancient pc and install win 95 on it. Or dual boot on your current pc with win 95 as an extra.

So I've had some limited success so far.

Borg works beautifully on VMWare running Win98. It runs in a tiny window but I can stretch it to fullscreen. It stretches it horizontally due to my widescreen monitor but that's acceptable.

Star Trek Encyclopedia works perfectly.

Fade To Black is a bit choppy. I need to tweak my settings.

Haven't tried In The First Degree yet.

No One Lives Forever 2 doesn't work when I try to run it natively but I think it's because I ripped the disks to ISOs and the copy protection is failing. I'll try it with the disc in the drive and maybe with a no-CD crack and see what happens.

I'm getting there! Thanks again for the help, everyone! Always a pleasure to talk to fellow enthusiasts.

Isn't Fade to Black a DOS game as well? Should not have problems with DOSBox.

As Foxhack said, the Creative disk games are all DOS as well.

I should have mentioned that the Creative disk games all run in DOSbox perfectly. Fade to Black is a more modern DOS game so it runs very slowly in DOSbox for me but maybe I need to tweak my CPU settings.

Yes, you probably do, unless you're running on a really weak system. If you can run any Build engine game (Duke 3d, Blood, etc) smoothly at 640x480, Fade to Black shouldn't be more demanding.

First settings to try modifying:
core=dynamic
cycles=max

Finding Win9x drivers for modern hardware is a problem, and you will still have the problems that the new hardware in itself brings (like games not liking multicore CPUs or higher frequency, or new graphics cards not supporting some legacy features).

So either keeping a retro-PC, or a virtual machine running in a modern PC, are the most probable solutions.

I'm sure to try VMWare now again, if they have really improved the Win9x support now.