Yes, no problem. Use XFDISK and it's Bootmanager. That's my typical setup.

2GB PRIMARY FAT16 DOS/WIN3X
2GB PRIMARY NTFS WinNT 3x/4x?
2GB PRIMARY FAT16 WIN9X
xGB LOGICAL FAT32 DATA (Games/Progs/Tools/Backups/Setupfiles/Drivers for Win3x/Win9x/WinNT

But you can do it differently if you like.

I usually boot DOS-Win16, Win98SE and Win2K or WinXP from such disks.

My partition table is:
#1 Win98 FAT32 nonboot starting at cylinder 1022 or 1023 to the rest of the disk.
#2 Win2K/XP NTFS boot starting at cylinder 64 containing bootmanager ,size 5507
#3 DOS nonboot FAT16 starting at cylinder 0 side 1, size 502
#4 DataExchange Extended nonboot & FAT16 logical starting at cylinder (767 or 768), size 2008

I do not max partition 3 to 512 and partition 4 to 2047 due to some problems with my Norton Utilities 4.5 Advanced Edition.
Logical partition order is different from physical partition order. The reason is that Win98 can see the DOS partition too but logical drive C has to have the upper partition entry in the table.
A copy of DOS and Win98 bootsector has to be stored in a file of the NTFS partition and added to the BOOT.INI file.
Win98 is happy with partitions above 8 GB, but needs to have its bootsector within the 8 GB limit (cylinder 1022 or 1023).

DOS can see partition 3=C and 4.1=D
Win98 can see partition 1=C 4.1=D and 3=E
Win2K/XP has partition 2=C and rest changeable

I find a boot manager like BootIt Next Generation/Bare Metal quite handy for this sort of thing. It lets you create more than 4 primary partitions, which can be selectively enabled or hidden depending on which OS is booted.

If you dropped one of the 9x OS's you could do it without any 3rd party software.

Install Dos/Win3.1 on a FAT16 primary partition.
Install Win95 it will ask if you still want to keep your dos/Win3 setup. It will then allow you to boot to previous OS
(Not sure if Win98 kept this feature, also not sure if you can install to a different drive?)
Install as many NT based OS's as you like and It'll create a boot menu. You can even install on a NTFS drive but of course the other OS's wont be able to access it.

Would I do it? no.
I like dual booting between 9x and NT and NT's boot loader does a good job.
But I don't like having to go into Win95 just to then go into dos.
Lucky simply booting into Win9x's underlying "Dos 7 mode" is more then enough for my dos needs on machines that also have some NT based OS.

dr.zeissler wrote on 2021-07-20, 11:50:

Yes, no problem. Use XFDISK and it's Bootmanager. That's my typical setup.

Disruptor wrote on 2021-07-20, 12:00:

I usually boot DOS-Win16, Win98SE and Win2K or WinXP from such disks.

astonsmith wrote on 2021-07-20, 13:54:

I find a boot manager like BootIt Next Generation/Bare Metal quite handy for this sort of thing.

chinny22 wrote on 2021-07-20, 15:13:

Would I do it? no.

No one mentioned if any of these will have an issue of actually seeing the large HDD itself? Don't older OS's have an issue with disk detection and max size limits?

PS: Chinny, it's not about convenience, it's more of "making a 90s OS museum" 😀

2mg wrote on 2021-07-20, 16:34:

No one mentioned if any of these will have an issue of actually seeing the large HDD itself? Don't older OS's have an issue with disk detection and max size limits?

That's the clou in my partition scheme.
DOS is doing well seeing its partition and the logical drive. It won't care about partitions above 8 GB.
The NT partition is complete within 8 GB too.
There is no trouble with the NT bootloader when having it within the first 8 GB, regardless which version.
NT can access the big partition of 9x.
The large partition from 9x can be used to install programs from 9x and NT too. And it can be used for CD images.

However, the BIOS should be able to see and access the large disk.
Some BIOS fail at 8 GB, some at 32 GB, some at 64 GB. Disks larger than 137 GB should be capped.

2mg wrote on 2021-07-20, 16:34:

PS: Chinny, it's not about convenience, it's more of "making a 90s OS museum" 😀

Yeh I got it was more a case of because I can then thinking you needed all the OS's for some reason, In which case I'd say just forget about dos and use Win9x's.

To keep things simple you want to keep any OS before Win2k below the first 8GB. Most OS's don't care about were the data partition is they just want to boot of a partition below the 8GB mark.
NT4 does work past the 8GB limit but you need to load the updated ATAPI.EXE from SP4 or setup will crash.
https://www.itprotoday.com/cloud-computing/ho … disk-larger-8gb
My cheat way to bypass this back in the day was to partition the remaining drive after NT4 was setup and service packed installed.

You also have the partition scheme to consider if you don't want to use 3rd party software.
NTFS is unreadable by Dos/Win9x
Fat32 is unreadable by Dos/Win3x/NT4 and below
FAT16 works in all OS's

Each OS will just ignore unreadable drives so it doesn't break anything, just reshuffles drive letters.

Buuut if it was me I'd avoid all this "fun" you say you have plenty of spare HDD's I'd get something like this and have something like a drive per OS. that way if you screw up an OS (or it commits suicide) rest of your installs are safe and sound
https://www.sotechdesign.com.au/5-25-swappabl … ide-bay-review/

Here's a copy of my self-notes when I did my multiboot setup.

NT4
• Must be installed in first 8GB of first disk

Win98
• Must be installed in first 8GB of first disk

Win2K
• Can be installed beyond first 8GB.

Boot Magic
• Needs to be installed on FAT partition in order to be visible from all OS. It's ok to start the install from Win98 on FAT32, but target directly needs to be FAT partition, preferably first partition on disk

Other Notes
• Installing on multiple drives is complicated with Boot SW, if you can switch boot drives with BIOS then do that, otherwise it's not easy. I did manage to install DOS and Win98 on one drive and XP on second drive and then use PLOP
• Installing multiple systems on one drive is relatively simple:
○ Hide all other partitions
○ Install OS within the first x GB of disk required by the OS on primary partition
○ Use boot manager of your choice

How I setup DOS6, NT4, Win2K, Win98 on one drive on Pentium Pro 200
1. Connect 1 HDD only during install to make things easier, after everything is setup attach additional drives as needed for more data storage
2. Install Windows 98 SE on FAT32 partition
3. Install Partition Magic 8
4. Create partitions:
a. Part 1: FAT, 1GB - for MS DOS
b. Part 2: FAT, 2 GB - for NT4, leave 2 more GB empty to later convert to 4GB NTFS NT4 partition
c. Part 3: FAT32, most of the disk space - for Win98, make sure it starts within first 8GB of drive
d. Part 4: FAT32, 4GB - for Win2K,
e. I like to setup partitions of different sizes to make it easier to identify what I'm installing where or when doing backups
5. Install Boot Magic 8 to Partition 1 (must be FAT) and configure it to:
a. Create boot entry for each partition
b. All partitions should be hidden from all other partitions
6. Reboot
7. Select partition into which to install, it will give an error that no system disk is found, insert bootable floppy or CD and install new OS. During install the OS will not see other operating systems already installed because Boot Magic is hiding them.
8. Repeat steps 6-7 for all OS
That's it.

You can ignor Dos, win3.x and win95 altogether. Just install win98 and the others.

Caluser2000 wrote on 2021-07-21, 11:05:

You can ignor Dos, win3.x and win95 altogether. Just install win98 and the others.

I don't want to! It's a 90sBox 😁
The point is to be able to enter any of these OS and be washed with blissful nostalgia and horrifying "oh god, the drivers, the BSOD, the IRQ/DMA".

Disruptor wrote on 2021-07-20, 16:46:

*

chinny22 wrote on 2021-07-21, 09:17:

Buuut if it was me I'd avoid all this "fun" you say you have plenty of spare HDD's I'd get something like this and have something like a drive per OS. that way if you screw up an OS (or it commits suicide) rest of your installs are safe and sound
https://www.sotechdesign.com.au/5-25-swappabl … ide-bay-review/

I'm actually having issues finding these on eBayou, it's mostly SATA, also only USA shipping, and also ATA-100 is the max of one I've seen... Tried all keywords, ATA IDE PATA 5.25 3.5 and so on.

p6889k wrote on 2021-07-21, 10:40:

*

Again, no-one mentioned if drive size would be an issue for any of these?
Sure, I need to partition them with something more modern-ish (XP onwards), but again, would for example DOS5 or DOS6 even see the proper partition on such a large disk?

What the OS can see depends on the combination of OS, disk controller and the BIOS. You didn't mention what HW you'd be using, but e.g. 386 era systems will usually not see more than 512MB, pentium 1 era systems may max out at 8GB, etc. No hard rules here, each system is different - to learn more you need to do some googling/reading. One way around limits with onboard disk controllers is to use add on disk controller with its own BIOS (must have its own BIOS) instead of onboard controller. E.g in my PPro200 I have Promise SATA 150TX2 Plus PCI card that supports large SATA disks, I usually don't go over 80GB as Win98SE has some limits here. In my 386 system I have Promise EIDE Pro add on controller that allows the system to see 8GB disks, with DOS 6 limit to 2GB partition, this allows me to setup four 2GB partitions. SATA controllers btw don't have 32bit drivers for Win3.x, so if you want Win3.1 and want add on controller, it will likely end up being an IDE or SCSI, not SATA.

If you already have your HW, i would recommend hooking up a HDD, lets say 80GB a then go to BIOS and see what does the BIOS see. If the BIOS sees e.g. only 8GB, you will need to figure out how to fit all your OSes into that 8GB, which is doable. Often even though the BIOS can see only 8GB, once you install a more modern OS, (i think Win2000), the OS itself will ignore BIOS limitation and directly see full disk size, up to the OS limit. I would however never recommend installing an OS on a partition that's beyond the limit of what the BIOS sees, even if the OS allows it. My experience is that it's going to cause a problem at some point if you try to use some disk utilities for partitioning, defrag, etc. so I just stay away from it. I don't remember all the details, just trying to give you some starting points to research/try further.

I usually try to keep my systems as period correct as possible with the exception of disk controllers to easily use large, fast, modern/reliable drives; and connect them to modern PC for backups for example.

If you're using more modern system, e.g. Pentium 3, 4, etc. (maybe even P2). You should be only limited by OS, the onboard controller will easily support 80GB + size HDDs. The BIOS may even support selection of boot drive upon boot without having to go to BIOS to change boot order, if you prefer to install OS on separate drives.

Caluser2000 wrote on 2021-07-21, 11:05:

You can ignor Dos, win3.x and win95 altogether. Just install win98 and the others.

Mixing long and short filesystems is a bit tricky sometimes, so no dos-tools in order not to destroy the fat.
Also you have to do some tweaks to start win3x inside dos7 (win98) or am I wrong here?

2mg wrote on 2021-07-21, 11:43:

chinny22 wrote on 2021-07-21, 09:17:

Buuut if it was me I'd avoid all this "fun" you say you have plenty of spare HDD's I'd get something like this...
https://www.sotechdesign.com.au/5-25-swappabl … ide-bay-review/

I'm actually having issues finding these on eBayou, it's mostly SATA, also only USA shipping, and also ATA-100 is the max of one I've seen... Tried all keywords, ATA IDE PATA 5.25 3.5 and so on.

According to the manual your motherboard only goes up to ATA-66 so 100 is fine, but your right don't seem to be many around anymore. I swear I did a search last year and they were still common!?

Physical drive size isn't a problem for the OS. It relies on BIOS for that so if BIOS detects the HDD fine then so Dos
Partitioning is done on the OS level so that's were the compatibility issues start.
EG you can create 30 2GB partitions on a 60GB drive. Dos would work happily with the first 24 then simply ignore the rest. In this case it would be due to no free drive letters but I think dos can happily go past its 8GB limitation its just a logical drive in an extended partition (never tried so not 100% sure)

p6889k wrote on 2021-07-21, 12:07:

What the OS can see depends on the combination of OS, disk controller and the BIOS. You didn't mention what HW you'd be using, but e.g. 386 era systems will usually not see more than 512MB, pentium 1 era systems may max out at 8GB, etc.
If you're using more modern system, e.g. Pentium 3, 4, etc. (maybe even P2). You should be only limited by OS, the onboard controller will easily support 80GB + size HDDs. The BIOS may even support selection of boot drive upon boot without having to go to BIOS to change boot order, if you prefer to install OS on separate drives.

Sorry, forgot to mention, it's a '99 PIII, so BIOS/MBO has no issues on that part, I was wondering if these OS could(n't) access it anyway due to some other limitation.

chinny22 wrote on 2021-07-21, 13:16:

Physical drive size isn't a problem for the OS. It relies on BIOS for that so if BIOS detects the HDD fine then so Dos
Partitioning is done on the OS level so that's were the compatibility issues start.
EG you can create 30 2GB partitions on a 60GB drive. Dos would work happily with the first 24 then simply ignore the rest. In this case it would be due to no free drive letters but I think dos can happily go past its 8GB limitation its just a logical drive in an extended partition (never tried so not 100% sure)

This is what I was looking for, as the BIOS/MBO I have work with large disks.