As I'm soon wiping my computer clean to install Windows 7, I had an idea of trying out some older operating systems on new hardware to see how the user experience is (especially regarding boot time and speed) nowadays.

Have you tried out older commodity OSs on modern hardware (few years old), such as

  • Windows 3.1
  • Windows 95
  • Windows 98
  • Windows ME

and what are your experiences - which of them would work? I would imagine that having several gigabytes of memory could be a problem for the older OSs, as well as hard drives over 32 GB.

  • Switched to CW. This is a discussion, not a question. – BinaryMisfit Sep 18 '09 at 9:28
  • ALl modern CPU's by intel and AMD still have real mode (a 16 bit mode with no virtualization still required by BIOS). And are technically backwards compatible with the 286 real mode and thus will run Windows 2.0, However the rest of the hardware may not be so nice, in particular the memory controller and the IDE controller, not to mention support for PCI is lacking in old systems (and ISA has been absent from motherboards for almost a decade now). – crasic Aug 7 '11 at 20:15
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    Great question. I would LOVE to install Windows ME on my new all in one touchscreen pc. Lol. Ahhh. Those were the days... – uSeRnAmEhAhAhAhAhA Mar 4 '14 at 15:27

11 Answers 11


I have Windows 98 in a VirtualPC on my home machine. I use occasionally it to run a Windows 3.1 era copy of MathCAD which just isn't happy running under XP, and to play a couple of ca. 1995 games that really want an early version of DirectX and can't handle XP either.

I also have a DOS 5 in a VirtualPC, left over from the steps required to get Win98 installed in the first place.

Edit: One advantage of a VM like VirtualPC for this is that you can easily present the ancient guest OS with an appropriately limited set of resources.

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    Another advantage is that you can easily migrate it between different computers (Hosts), especially if the disk image is small (say 512MB for an ancient dos system). – crasic Aug 7 '11 at 20:11

I've successfully run Windows 3.11 for Workgroups with DOS 6.22 on a spare 2Ghz Celeron machine I have. Had to install a seperate TCP/IP stack for network support but using IE5 I did manage to get the little thing on the internet. :-)


If you have any sort of virtualisation product installed, there is no limit!

I have messed around with Windows Disk Operating System (before it had a version number!), and many other systems that are 20+ years old.

If you are willing to take out some RAM, you can get Windows 3.1 working no problem on modern hardware - It will work with the extra RAM, but HIMEM.sys can take an age to complete on a high end modern system!

I know you can go earlier than that, but without any sort of hack and just the standard disks, I think that Windows 3.1 / Dos 6 is probably the easiest to install early OS that anyone can mess around with.


OS/2 Warp is still around (as the commercial OS eCommStation) and works fine with modern computers

not exactly Windows but much of the 'code base' is assumed to be similar :)

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    OS/2 was wildly different from Windows 3.1. So much so, that it required a copy of 3.1 to run Windows software. OS/2 shipped with a 16 bit DOS, which would run in an emulator, but OS/2 itself was a 32 bit, true multitasking operating system; not at all like any of Microsoft's offerings at the time. Even DOS applications didn't always run, due to developers using undocumented API calls assuming the machine would run MS. – Richard Hoskins Sep 18 '09 at 16:18
  • OS/2 is not Win3.1 similar, but a product that IBM and Microsoft were working together to replace it. MS dropped out, and used some of the ideas as NT. OS/2 was marketed as a better way to run Win 3.1 apps, with better isolation than Win95. – Rich Homolka Feb 10 '12 at 21:09

I recommend giving Windows NT a bash in a VM - it's astonishing how fast Explorer feels these days :)


The easiest way to run such an OS is to use a VM. I've run Windows 95 in a VM with almost no problems. Unfortunately, the network card was nowhere to be found, so no internet for me. Windows 98 and up should not be such a major problem.


Would you be happy to just see a successful install?
Or, would you also want it to be usable for daily activities?

The primary problem I see with such exercise is the lack of driver support for older Windows versions.

If you use a VM platform the driver problem might get resolved to some extent.

If might be more fun to check out some Linux distributions
(which btw you can do even with USB booting flash drives).

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    I would be happy to see a successful install and fooling around a bit, but it wouldn't have to be really productive. – simon Sep 18 '09 at 7:47

Why not run the oldest computer ever on it? (Not strictly an operating system)


One problem you're going to have with older OS's are hard disk and disk controller drivers. I'm assuming that your 2007+ PC has SATA hard drive(s) rather than the older IDE/PATA drive interface?

Even Windows XP with the latest service pack can't detect SATA drives at setup unless you either switch your hard disk controller's mode (in the BIOS) to its Legacy IDE compatible mode, or load your SATA controller drivers from a floppy disk at the "Press F6 to load RAID drivers" stage of setup.


I guess Windows 98 did not have (much) USB (1.1, 2.0) support. The father back you go, the more hardwaresupport you'll lose, the smaller the Diskdrives have to be.

On the other hand, I booted a win2.0 from a PC in 1998, and it was pretty fast, nearly instantly up. :)


Windows 2000. Older versions did not support hard disks >128G (and SATA btw). (you need to modify the Win2k install disc to get support at install)

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