Best way to play old games that require Windows 98/XP?

I’ve simply installed Windows XP in a guest virtual machine (VMWare, Hyper-V) and that’s been that. Hyper-V will require a Professional version of Windows, but the VMWare Player (you don’t need Workstation) is free and will work just fine.

I play even Windows 3.1 games that require 16-bit libraries just fine. Nothing special. Install and go. Maybe a bit of ye olde config for really old DOS games where you had to set up a sound card in a separate config tool from the game :). Some games may require you to right-click on the executable, go to Properties, and set the Compatibility Mode to an older version of Windows. This is built into XP itself. Honestly, I think I only have 1 or 2 total games that have ever required it.

Been doing this forever (15 years?) on both Intel Macs and x86 desktops for as long as I can remember. Moreover, this isn’t just my old memories — literally played a Windows 3.1/95 game (came out in 1994) this weekend while watching Le Mans.

What are some of the games you're having trouble with?

You could try Steam's Proton, which is based on Wine but has a lot more compatibility work done on top. You might even find your games in https://www.protondb.com/ to see if someone else has tried them first.

So the biggest issue you will find is that the standard virtualization platforms like VMware and Hyper-V aren't suited to this: Many games need support for extremely old DirectX versions and that generally isn't implemented for things like VMware especially prior to XP.

PCem is the one I've seen that seems ideal to the task, but I haven't had the time recently to experiment with the configurations for it.

https://www.pcem-emulator.co.uk/

The key distinction is that it actually emulates various legacy graphics and sound hardware that games may have been intended to run on.

There's a whole generation of games from the mid to late 90s (and perhaps into the early 00s) that's remarkably annoying to play these days because of this issue. The game I've personally tried to get running, every once in a while, is Mechwarrior 3, but it's a complete disaster. The last time I tried to run it, I actually managed to load into the first mission, but the in-game physics were remarkably broken, with the amusing result where the first enemies you face in the game (a couple of little tanks) drove up towards me, hit a little bump, and then immediately rocketed into the sky.

At least part of the issue is that the game uses multiple threads, but was designed for systems with a single CPU, with a clock speed that's considerably slower than is present in modern systems. Something about this difference in timing breaks the whole thing in ways which are diverse and inexplicable.

Now, this comment thread contains plenty of possible solutions I could attempt, but if it's really a matter of the game relying on something like the CPU speeds of contemporary hardware (not to mention contemporary graphics hardware) then I start to think that I'd need to track down some kind of Pentium 3-era gaming PC to really make it work.

Wine may still be the way to go. You should check the logs, if you haven't already. If the crash occurs because of missing runtime libraries, the issue might be fixed with Winetricks. https://wiki.winehq.org/Winetricks

If you have Windows 10 Pro, Hyper-V[1] might work better than VirtualBox. I'd check why VirtualBox crashed, though. It's possible you don't have virtualization enabled in your bios.

1: https://learn.microsoft.com/en-us/virtualization/hyper-v-on-...

Maybe PCem, as demoed on https://www.youtube.com/watch?v=mWEE2RJj3YI

VMWare Workstation Player is free.

https://customerconnect.vmware.com/en/downloads/info/slug/de...

Your virtualbox crash is likely due to bios/uefi configuration.

Booting from a USB is also a valid route to a solution.

https://86box.net/

Is pretty good for running old OS like Windows 98 SE.

You could try BoxedWine. It is enough of a PC emulator to run an unmodified 32-bit version of Wine. Runs on Windows, Mac, linux and in a web browser.

- https://github.com/danoon2/Boxedwine

- https://www.boxedwine.org/

As a Wine user (... a winer?) I'd like to go over a couple tips which you may already have tried, but which can help if you aren't used to them:

- did you create a 32-bit prefix?

- did you try setting the Windows version to an older one, like Windows 95?

- did you try using something like InnoExtract (if applicable) to extract the game data without running the installer?

I would like to thank everyone for contributing. There are way too many approaches to try them all, but my further research led me to the following conclusion:

  I'm going to start with trying Windows XP on either VMWare Player or qemu

  Most versatile / reliable source for Windows XP isos here[1] (needs registration)

  Trying this[2] modern installer creation may be a next step

  If this does not work, I'll try Win 98 SE on dosbox-x following this[3] guide

[1]: https://forums.mydigitallife.net/threads/microsoft-windows-x...

[2]: https://forums.mydigitallife.net/threads/tool-xp2esd-create-...

[3]: https://dosbox-x.com/wiki/Guide%3AInstalling-Windows-98

If they are old enough to work without hardware video acceleration, then XP inside qemu works. I have several old games that are incredibly far from working in wine, and I have run them this way. They are all late 90s though, and games from that era mostly will work without hardware video acceleration.

You can try dosbox-x. It was forked from dosbox a while back and has enough compatibility to run Windows 98. (Regular dosbox 0.74 was released in 2010.)

On Linux, have you seen the Lutris project?

It's basically a launcher for games, and the community maintains Wine/DOSBox/etc configurations.

Semi-related, though also nearly impossible to setup these days: Windows 7 Pro supported "Windows XP Mode" using Virtual PC.

https://archive.org/details/windows-xp-mode_20200907

Never underestimate the convenience of just keeping an older computer around...

Try installing windows 95 in dosbox and save that as a base image for your software.

Don't know if this was o e of the "tricks" you tried... anyway worked for most old games that required windows I tried

I've been porting this to Nixos all week. Handles glide emulation pretty well

https://github.com/kjliew/qemu-3dfx

I'm not an expert but Dosbox can be run in browser.

I've seen entire oses in browser too, but that would be too much CPU to waste. Anyway, if your game is dos based that could help you.

I've had pretty good luck with Virtualbox and legacy OSs. It's open-source. WINE works surprisingly well with older Windows games and apps too.

Copy the installed version, and run that with wine.

What about installing Windows 98 in dosbox? I haven't tried this but have done it with Windows 3.11.

This was the first result when I searched: https://dosbox-x.com/wiki/Guide%3AInstalling-Windows-98

Build / buy an old enough computer.

Did you look at the wine appdb for your games? There might be some things you can do to get it running.

It's a long shot, but some old games are available via https://www.scummvm.org/

It really depends on the game (particulary old DirectX <5 and are PITA).

Without the game name and it's requirements I only can advise to seek advice on Vogons or Old-games.ru

Wine