How-to Install Win 3.11, Win95, Win98 and Win2000 on the same MBR disk

Preamble :

I recently had to start my very old laptop to open a WPK file ( that is the original Wordperfect file format ) using the program installed under Windows 3.11. Which made me reflect a little about that computer. So here is something from memory lane.

Nowadays I only run Window 10.

But I also keep an aged laptop running Window 7 and Windows XP. It doesn’t see much use, frankly. But better safe than sorry so I keep it.

And I keep an even older laptop from around 2000 running Windows 3.11, 95, 98 and 2000.

Uncommon Disk Configuration :

Having a single computer switchable between those four old OS’s is not common. And it also requires a special partitioning scheme that Microsoft actively disapproved stating it would give trouble and did not support doing. I haven’t experienced any trouble.

The key to allow this is partitioning the hard drive with four primary partitions.

In those days most disks was IDE disks ( contrary to now SATA ) and the disks used the MBR disk initialization scheme ( contrary to now GPT ). The disks sold those day could be as small is 6GB. The sweet spot disk size for this setup is 40-80 GB. Odd problems could arise using disks larger that 128GB so don’t do that.

It can be difficult to find a utility that allows doing this special partitioning. But companies like Paragon and Acronis had disk utilities that supported doing this off a boot CD. I used such tools.

While writing this, I googled the subject and found a link to a free utility which claims to support generating multiple primary partitions.

See here :

Otherwise you could mount the disk in an external enclosure to do this. If you have an older Mac then Disk Utility can be used.

Disk partitioning could/should be done before installing any OS. Just in case something should go wrong.

How to select the OS to boot :

The tool used to switch between which partition to boot from is the very basic tool FDISK.exe which was included in all DOS versions. You select which partition should be Active next time you boot. Simple as that. Windows 2000 has a GUI to set the Active partition but the principle is the same. Notice though that FDISK with DOS 6.22 ( Windows 3.11 ) can see and select all primary partitions but it doesn’t know what is on the partition and it also reports the partition size wrongly. But selection works.

No need to install any fragile custom boot manager or anything. Any computer savvy person can do this.

Using this concept has the very nice property that the active disk is always given drive letter C:. The drive letters for the other partitions were mangled in a way only Microsoft could explain. Or maybe they could not.

Remember that Win 3.11 could only install on FAT. 2GB max. And it could not understand any newer partitions like FAT32 nor NTFS. So one such partition should be made. I made it the first partition on the drive. Some also claimed technical reasons for why a FAT partition should be created first.

The next two partitions were for Windows 95 and 98. They also supported FAT32 but not NTFS. So FAT32 were used. 4-8 GB were the sizes I choose.

Finally a partition for Windows 2000. It supported the older partitions and NTFS. I preferred to use FAT32 because then Windows 95 and 98 could use drivers located on that partition. So this partition was the largest. Which was nice as it could also be storage for backups for the older OS’es.

Installing these OS’es requires old hardware. Old hardware is not supported well by newer OS’es. In particular, don’t install Windows XP instead of Windows 2000. It might install but will disappoint because it really requires faster hardware.

Installing and Round-Up :

All four OS’s were fully independent and did not rely on each other. So once the drive were partitioned then each OS could be installed in any order. The benefit of that fact was that it was also easy to backup each partition to support recovering from system corruption often occurring when installing drivers for the three oldest OS’es. Windows NT backup was very handy for this.

I strongly suggests that a partition backup is done after every driver installation with the older OS’es. If a driver installation fails, and it often does, then your installation on that partition could be in an corrupted state. Being able to recover/restore is a major convenience. Always restore and try again, if something unexpected or unexplainable happens during driver installations.

Then it was time to actually install an OS. While partitioning the disk one should also have made the decision which partition to boot from. Which OS to install first. Suggestion is starting with Windows 2000 to have the backup utility ready when installing the older OS’s afterwards.

There is essentially nothing more to this subject. The concept described is very robust contrary to Microsoft’s officiel dual-boot concept which often corrupted the OS’es if anything unexpected happened.

Well, maybe one more advice. Do yourself a favour and install a dual pane file manager. For DOS it would Norton Commander or a similar free tool. For Windows it would be Windows Commander ( ). Life is so much easier using these tools during the driver installation phase.

DOS Boot CD :

It is nowadays possible to boot to DOS from a boot CD. Using a boot CD instead of a floppy disk gives a boot speed advantage. It also allows to boot a system that does not have a floppy drive at all. That was the case for several laptop models from around year 2000. Those laptops were sold with an external floppy drive that connected using either the printer port or an USB port. Fortunately the BIOS for those machines often also supported booting off a CD :

Look here for ISO images :

Start Menu for Windows 3.11 :

You can actually download a program called Calmira II that gives Windows 3.11 a start menu like Windows 95. That is the coolest thing I have seen for years :

Look here for info :

Laptops from around year 2000 :

What is a usable laptop from year 2000 to implement this four OS scheme. A relevant question as they cost next to nothing if they can be found.

There are three essential qualities for such a computer :

  • It must have a proper graphics chip. The ATI Rage or derivative is a good starting point. Besides having Windows drivers for Win 3.11 and newer it also supported DOS graphics.
  • It should have a proper sound chip. The ESS Maestro in some variant is a good starting point. Besides having Windows drivers for Win 95 and newer it also emulated Sound Blaster Pro in DOS and Win 3.11.
  • It should have a BIOS setting to expand the display to full size in text DOS. Otherwise the DOS display will only cover the central part of the display which looks silly.

Using USB for anything pre Windows 2000 is hit and miss, except for an USB mouse on Windows 98. These old laptops usually had only one USB 1.1 port anyway. Be sure to have backups before trying to install USB drivers.

Examples of compatible laptops includes : Compaq Armada M700, HP OmniBook 6000, Dell C600 and IBM ThinkPad 20-something. They are rare, fragile and probably ugly. And they were expensive when new.

As a compromise there are still plentiful of ThinkPad 40 and 41. The ThinkPad 40 and 41 are quite simple to install if they are fitted with the Radeon 7500 chip. The ThinkPad 41 with a Radeon 9000 chip can be used for Windows 95 using a UNIVBE display driver. But it only supports generic 16 color VGA for Windows 3.11. And there is no sound support in Windows 3.11.

The best ( in the meaning of giving the fewest complications ) computer to configure for a four OS setup would of course be an old desktop computer with a Tseng ET4000 graphics card and a Creative Sound Blaster sound card.