Installing and playing Windows 98 game on Windows XP - what's the worst that could happen?

So I know that a Windows 98 game isn’t likely to work on XP - but, since I have the game, I might as well try.

I’m not so much concerned that the game won’t work (if it doesn’t, it doesn’t,) though, as I worry it might cause system damage. Would it cause a crash?

The game might crash but Windows probably won’t. (Note the word “probably”)

Back in the day, there were two basic versions of Windows, the original version which was backwards compatible to DOS, and NT. These two operating systems looked very similar, but were fundamentally different in the way that they were structured. NT has what it calls the “hardware abstraction layer” which completely prevents programs from directly accessing hardware. Original Windows does not have this structure, and instead allows programs to directly access hardware if they want to.

The original Windows is version 1.x, 2.x, 3.x, Windows 95, Windows 98, and Windows ME. If you look at how Windows identified itself the versions become a lot clearer. Windows 95 is Windows 4.0, 98 is 4.1, and ME is 4.9.

NT versions are Windows NT 3.1, NT 4.0, Windows 2000 (NT 5.0), Windows XP (NT 5.1), Vista (NT 6.0), Windows 7 (NT 6.1), Windows 8 (NT 6.2), Windows 8.1 (NT 6.3), Windows 10 (NT 10.0).

Again, looking at the version numbers makes it a lot more clear about exactly what is going on. Windows 7, 8, and 8.1 weren’t really major changes to the operating system under the hood. While the user interface looked a lot different, the actual guts of the operating system did not change that much. With Windows 10, people were starting to pay more attention to the version numbers so Microsoft got rid of useful version numbers and let the marketing folks decide version numbers as well as OS names.

Home software, especially games, often accessed the hardware directly. Sometimes this was for backwards compatibility so that you could continue to use your old DOS programs. Sometimes it was for performance. Games would often bypass the operating system completely and would directly control the video card, for example. If they didn’t, then the games would not have run fast enough on the technology that was available back then.

Business applications often ran in networked environments with multiple tasks running, and in this environment, the HAL really proved its worth. So there was this natural divide where Windows was for home users and NT was for business users.

Microsoft got a little tired of maintaining two different Windows lines (original and NT), so they decided to “merge” the operating systems. This was pure marketing BS. They didn’t merge anything. What they wanted to do was kill of the original Windows line and force everyone to NT. Marketing BS aside, this was actually a good thing, as the HAL does tremendous things to prevent misbehaving programs from trashing your system or trashing other programs. So it’s actually a good thing that we’re all running NT at this point.

The big problem was that a lot of software, especially games, was written to directly access hardware so that the games could run fast enough on the available technology. And since the HAL didn’t allow this, those games would not run under NT.

Microsoft first tried their “merge” with Windows 2000. You could see evidence of this with some of the cutesy icon name changes between NT 4 and 2000 (My Network Neighborhood, for example). About halfway through development, Microsoft realized that this “merge” was going to fail miserably. There was just too much common home software out there that would not run under NT. But Microsoft did announce their intent to kill off Windows and force everyone to NT, and all of the software developers took notice. They put Windows 2000 back on the “business” track and abandoned plans to market it for home users, and rushed Windows ME out the door so that they would have something to sell to home users (which is why ME was such a buggy piece of crap when it first launched).

Microsoft successfully completed their “merge” (aka killing off Windows completely without actually merging anything) with Windows XP. What is important to note for this discussion is that games that wouldn’t run under Windows 2000 usually wouldn’t run under XP either. The only thing in Microsoft’s favor was that all of the newer software was designed to run on NT, and the games and programs that didn’t run under NT were now older and not as widely used.

So, what does all of this mean for OS and software compatibility?

You get into the biggest trouble when you jump OS lines, meaning going from any of the original Windows operating systems (95, 98, ME) to any version of NT (2000, XP, Vista, 7, etc). Your next biggest trouble comes from jumping major versions (i.e. XP to 7 since this is a change from Windows 5.x to 6.x). Jumping minor versions (Windows 7 to 8.0 for example) can break things but it’s not as likely.

98 to XP is a jump across Windows lines (Windows to NT) and is also a major version jump (4.x to 5.x), so depending on how the game was written, it might not run at all. The game also might not even install.

As far as what’s the worst that could happen, the worst that I have personally seen is that the game locks up the computer’s user interface, forcing you to completely reboot the computer. Theoretically I suppose it’s possible that the program could damage your installation of Windows, but I personally have never seen it happen and also have never even heard of it happening to anyone that I knew.

There’s no real risk of hardware damage. The HAL in XP should prevent even the worst misbehaving program from even accessing the hardware, let alone getting it into a state where it could theoretically damage something.

If this ancient XP computer still has an old fashioned CRT type monitor, you can damage the monitor by having the game switch into a resolution mode that the CRT wasn’t designed for. It won’t blow the monitor right away, but the extra strain on the CRT could cause it to die an early death. Modern monitors are immune to this.

If it were my system, I’d just try it and see what happens. Half the time the program will run anyway even though it wasn’t designed for NT. Even if the program doesn’t work, the worst that I would expect to happen is that the computer locks up and you have to hit the reset button. It’s much more likely that the program just won’t install or run.

tangent: Win95/98 virtualizes the memory and the I/O address space, allowing one application at a time to control the hardware I/O space and memory mapped devices. This acts the same as ‘allowing direct access’, but it’s not. It’s virtualized the same as WinXP (using a different architecture). The difference is that (by default) Win 98 includes a ‘driver’ that maps the virtual I/O space to the real mode I/O space, and (by default), WinXP does not.

What’s the worst that can happen? Try to imagine all life as you know it stopping instantaneously and every molecule in your body exploding at the speed of light.

The OP may wish to look into virtual machines and/or emulators. Sometimes that sort of thing is the only way to run really old software.

Speaking of which, there’s a ton of old dos and early windows games (and other software) out on (and other places) that you can play in a dos box right in your browser.

Online Classic Games is a good site.

It includes hundreds of old console games that you can play in your browser, as well as DOS and Windows games.

A couple of minor points. @engineer_comp_geek covered things very thoroughly in his excellent post. It’s true that a secure protected kernel and virtual address spaces in user mode were key to the stability of Windows NT compared to the home versions of Windows prior to XP, and that the HAL can be regarded as the method of implementing that functionality, but that’s more or less coincidental. Any OS running on hardware that supports a privileged kernel mode and a non-privileged user mode with virtual addressing can support that kind of application isolation and protection of the kernel and I/O space. The real purpose of the HAL was to provide a modular architecture for platform independence. The original versions of NT were targeted in principle to DEC Alpha, Itanium, MIPS, and PowerPC platforms in addition to traditional Intel x86/x64 architectures. That platform independence ultimately turned out to be far less important than had been anticipated.

Another point is that the DirectX gaming API goes back to Windows 9x (actually even earlier, but it became recognizable in its present form with Windows 95). If the game was written to use DirectX, and if Microsoft maintained any decent semblance of backward compatibility, then there’s some chance that the game might actually work. However, IIRC, DirectX was not very widely used prior to Windows XP, or at least, certainly far from universal.

All of that said, I think it’s extremely unlikely that the game could damage anything, and more likely will just not install or not run.

Windows XP does include something of that nature, although I confess that if I ever understood how it was implemented I certainly don’t recall it now. But the fact is that you could literally run an old DOS game in Windows XP with some reasonable chance that it might work, despite the fact that it expected to have direct control of all I/O. I’m pretty sure that I was able to run the venerable “The 7th Guest” DOS game under XP. It’s certainly true, as e_c_g said, that XP was in no sense a “merger” of Windows 9x and NT – Windows 9x code was quite properly thrown in the garbage where it belonged. However, Microsoft did go to great lengths to achieve a functional merger by adding a lot of features to XP that made it friendly to home users and gamers while retaining as much as possible the security and stability of NT. This was a marvelous feat of software engineering and was very hard to do, which is why the effort to make Windows 2000 the first universal OS for both business and home ultimately failed. There just wasn’t enough time for that ambitious an undertaking. To this day I think Windows XP was Microsoft’s greatest achievement, other than Windows NT itself, and everything after was just incremental or even sometimes regressive.

Windows 98 games are actually rather likely to work on Windows XP. I would say it’s a decent bit more than half. Microsoft went to a lot of trouble to try and maintain compatibility. It might work out of the box, but, if not, be sure to try Compatibility mode, which was first introduced in Windows XP. Right click on either the .exe file (for the installer) or the Shortcut (for the game itself) and try out the various options under the Compatibility tab.

Or you can also try to force the Compaibility Wizard to come on:

  1. Click the Windows “Start” button and select “Control Panel.”
  2. Click “Programs” and select "Run programs made for previous versions of Windows " under the Programs and Features section to launch the Compatibility Wizard.

You can also just use Google to check and see if the game is compatible with Windows XP, and whether you need to do anything special to get it to work.

If you can’t, then, yeah, using a virtual machine is probably the way to go.


I won’t say that compatibility mode is completely useless, because on rare occasions it can make a program work, but in my experience, its success rate is extremely low. It’s worth trying, but don’t put too much faith in it.

I am a packrat, I tend to upgrade Windows in place and keep old games around forever. I have files on my computer from the mid 1990s. IIRC Windows XP was nicely compatible with Windows 98.

Really Windows had a good record of backward compatibility until they discontinued 16-bit support in 64-bit versions of Windows. That mostly affected old DOS utilities I used, like (not a website, an executable file.)

Compatibility mode has worked well for me in running a few picky games that didn’t like Windows 10. I haven’t needed to use it a lot, but it succeeded more than it failed.