How to Install Windows 98 on Steam Deck

This guide really only exists due to my own stubbornness. My brother and I used to crush Sid Meier’s SimGolf back in the ‘00s. I remember it being a pretty fun and relaxing experience, even if I never got very far before bankrupting myself by designing what was probably the worst golf course ever created. But still, I wanted that sweet nostalgia hit and surely it couldn’t be that hard to run on a modern system… right?

Turns out: trying to run SimGolf on modern systems absolutely stinks. I sank more time into this than I probably should have and SimGolf proved to be just as stubborn as I was. I tried Proton, Protontricks, WINE, Bottles, x86Box, PCem, Heroic, Lutris and even attempted to splice it into known working game wrappers. PCem and x86Box came very close, but the performance wasn’t quite where I wanted it. I was ready to give up when I remembered RetroArch has a DOSBox core that can run Windows 95 and 98. Digging into it further, I found there was a standalone fork with Linux support called DOSBox-Pure Unleashed. After getting it setup, I’m happy to say I’m on my seventh hole and my golf course is thriving. It might not be 100% perfect, but it’s probably 95% of the way there.

Using DOSBox-Pure Unleashed, you can get Windows 98 installed on the Steam Deck and run your older Windows 9x games surprisingly well. I get it, this seems a little silly. But, if you think of it more of a launcher than a lightweight Virtual Machine, it makes a bit more sense.

Installing Windows 98 on Steam Deck with DOSBox-Pure Unleashed

Disclaimer: Not every game will run flawlessly, which is simply a limitation of emulation. If there’s a native or simpler way to run your game, I’d highly suggest that instead. This guide will also work for Windows 95, simply swap in a Windows 95 ISO.

1. Swap to Desktop Mode on your Steam Deck.
2. Download the Linux x64 build of DOSBox-Pure Unleashed from their Github page.
3. Place the executable in your preferred location.
   
   I went with with: /home/Games/
4. Download a Windows 98SE ISO, I went with an OEM version.
   
   You will also need a CD key
5. Run the DOSBox-Pure Unleashed executable.
6. Select Load Content, navigate to the Windows 98SE ISO and select it.
7. Select Boot and Install new operating system and choose your desired hard drive size.
8. Follow the prompts to install Windows 98.

It takes a little while for Windows 98 to detect and install the required drivers and software, but once finished you’ll have a functional install. It’ll behave exactly like it did back in the day, so remember to shut it down when you’re finished and treat it gently so it doesn’t shit the bed like it used to.

To access the on-screen menu (to change settings or quit the application): the default hotkey is Ctrl+F12 or the middle-mouse button.

To launch Windows 98: launch DOSBox-Pure Unleashed and select Run Installed Operating System and select your Windows 98 install.

To use DOSBox-Pure Unleashed in Gaming Mode: right-click the executable and select Add to Steam. Next, we’ll look at transferring games, files and applications into the OS.

How to Add or Install Games or Applications in Windows 98 within DOSBox-Pure Unleashed

Disclaimer: If you need to add multiple installers or files, the best way to do this is place everything you need into a single .ZIP file. For multi-disc games, it’s best to combine the discs into a single ISO or install a compatible disc mounting application inside Windows 98.

1. Run DOSBox-Pure Unleashed.
2. Select Load Content and select the .ZIP or ISO file you want to mount.
3. Select Run Installed Operating System.
4. Once Windows 98 boots, the .ZIP or ISO file will show as a mounted disc drive.
   • For ISOs, run the installer from the disc drive.
   • For .ZIPs, open the disc drive and run your installer(s) or copy your files to the C: drive.

To add more files or install additional games, you’ll need to repeat this process. Shut down Windows 98 first, then mount your next .ZIP or ISO using the Load Content function.

RetroArch Core and EmuDeck

If you’re like me and use EmuDeck, you can complete a similar setup as using the RetroArch DOSBox-Pure core.

1. Swap to Desktop Mode on your Steam Deck.
2. Download a Windows 98SE ISO, I went with an OEM version.
   
   Again, you will also need a CD key
3. Navigate to your EmuDeck install directory and head to the /roms/dos/ folder.
4. Place your Windows 98 ISO, along with any other ISOs or .ZIPs here.
5. Open EmuDeck, or ES-DE, and scroll to MS-DOS.
6. Select your Windows 98 ISO.
7. Select Boot and Install new operating system and choose your desired hard drive size.
8. Follow the prompts to install Windows 98.

A few notes:
I recommend using the on-screen keyboard for the initial setup. I ran into issues entering the Windows CD key with a physical keyboard. You can toggle the on-screen keyboard with L3.

Press L3+R3 to bring up the RetroArch menu, you can adjust any DOSBox-Pure core settings here.

To launch DOSBox-Pure through the MS-DOS section in ES-DE, you’ll need something for the emulator to run or mount. Any ISO, .ZIP, .EXE will do the trick. Alternatively, you can open RetroArch directly from the Emulators section, select the DOSBox-Pure core and run it. Select Run Installed Operating System, select your Windows 98 install to boot into the OS.

The DOSBox-Pure core can also run DOS games directly. Simply place zipped DOS games into the /roms/dos/ folder and launch them from the MS-DOS section in ES-DE, choosing the correct .EXE to launch.

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Further Notes

Controls

As with any non-Steam game or application, you’ll need to configure your own controls. Since you’re effectively running a full operating system, I would suggest setting them similarly to the Steam Deck’s Desktop Mode.

Of course, your setup will depend on your own needs and what you’re planning on using the OS for. DOSBox-Pure also has its own gamepad control settings, which you can tweak to your liking.

Performance

DOSBox-Pure is emulating some super old hardware, it may not be the most authentic experience if that’s what you’re after.

Most Windows 9x-era games are going to run perfectly fine, but it’ll likely struggle with more demanding titles from the late ’90s and early ’00s.

You can also use the settings within DOSBox-Pure to tweak the system to your liking. You can choose different CPUs, RAM, video memory, shaders and almost anything you could think of. Play around and see what works best for you.

An optional step, the Github suggests downloading and installing the Voodoo graphics drivers for Win9x. Specifically V3.01.00, I found it made no difference. But, go ahead if you feel the need.

Multi-disc Games

I briefly mentioned these earlier. Multi-disc games can be a pain with older operating systems. You can either combine these into a single ISO for ease of use, or install a mounting tool within Windows like Daemon Tools. For these older titles, I would recommend putting the ISOs into a .ZIP file, importing them into the OS and using a disc mounting tool.

File Storage

Everything you install or import into the OS will be stored on the virtual hard drive you created during your Windows installation. Any additional files can be added using the Load Content method outlined earlier and deleting files is handled directly within the OS. Make sure you choose a virtual hard drive size with enough headroom for the games, files and applications you plan to install.

Stability

Windows 98 was never the most stable operating system and this virtualised version running via DOSBox is no exception. Crashes shouldn’t happen frequently, but they’ll likely happen when you least expect.

As always: save early, save often.

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Running Windows 98 on the Steam Deck might seem pretty ridiculous, but DOSBox-Pure Unleashed makes it surprisingly practical. Once everything is setup, it actually becomes a pretty great way to launch and play older Windows 9x games directly on your Steam Deck. If you want your ’90s and early ’00s classics in one simple launcher, this setup works incredibly well.