Multi Booting DOS-w3.1, w95, w98 and ME

Firstly, I apologise if I've posted this in the wrong category, but Software seems appropriate.

I own numerous old PCs running a mix of DOS-w3.1, w95, w98 and later.

More out of curiosity than anything else, I've been doing some testing on multi booting w9x to see what's possible.

I've found it is possible to multi boot combinations of DOS-w3.1, w95, w98 and ME (dual, triple or quad boot versions) although depending on the number of OS's to be booted, there are a few quirks to be overcome.

So far I've been able to:

* Dual boot w95 and w98 (no boot manager used)
* Quad boot w3.1, w95, w98 and ME (no boot manager used)
* Quad boot 4 installs of w98 (no boot manager used)
* Triple boot w95, w98 and ME (using shareware BootitNG)
* Quad boot w3.1, w95, w98 and ME (using free OSL2000)

Generally, the more OS's added to the mix the more quirky it becomes, due to w9x versions over-writing each others boot files.

Using a boot manager such as OSL2000 simplifies things, but it's still possible to multi boot without a boot manager.

DOS-w31 adds another complication as w9x installers insist that partition 1 for their boot files be FAT32 and not FAT16, but this can be overcome.

Multi booting w9x with later Windows versions is simple as these OS's are multi boot aware.

I've been testing out various combinations of w9x using VirtualBox 6.1.26.

I've uploaded some example VHDs to the internet archive if anyone is interested.

In the archive's Software category, search for shotter_nail to see the uploads.

If anyone has any questions about multi booting w9x I'll be happy to give whatever help I can - but just be aware that I don't spend a lot of time on the net and will probably only check in once a week.

Kind regards,


  • Hello everyone,

    I thought it may be helpful if I created a small web site that details some lessons I've learned about multibooting various Windows versions and also with some details of 2 boot managers that I've tried (OSL2000 and BootitNG) as part of the learning curve.

    I hadn't posted anything about my experience in this on the Internet Archive site but I thought it may be helpful to put a link here as it may save someone else from encountering some of the problems that I ran into.

    The website I've created is a small site (rather crudely done as I don't know html) running on my Synology NAS and the link to it is:

    Hopefully some of the information will be of use to someone interested in multibooting w9x.

    Kind regards,
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