Microsoft BASIC on the Dragon 64 borrowed from my grandfather.... the first computer that I ever used!

dont know if it counts as an OS, but you could use the BASIC interpreter to launch games etc. in addition to writing programs

I got a laptop with 3.1 on it when I was young.
In a VM, probably XP Home. I haven't got the 3.1 disk/drive anymore.

MS DOS was my first MS OS on IBMs

Microsoft Minus One o; Ancient.

I think the oldest I have used is DOS 3.3 on my old Amstrad PPC512.

Windows NT 4.0
About a year ago I got given a Acer Extenza 367t or something like that running windows 98SE with 80 MBs of ram and a 2 GB hard disk..After a while I downgraded in favor of Windows NT 4.0 because it was more stable and I preferred it.Later on I decided to put windows FLP on on it and then I put Windows 2000 on it.In about january this year the hinges broke and my dad did not want to fix it...so he threw it out.I still hate what he did to this day.

On Real Machine : Win 98 SE.
On Virtual Machine : Win XP [when i started using Win Vista , win 7 ][ Didn't ever try Old os like win 95 and earlier on VM or RM

Oldest OS that I used on real PC was Windows 95 and on Virtual PC i was playing old DOS games on MS-DOS-6

First Physical Windows: Windows 95 B
Oldest Windows Used/tested/played around with: Windows 1.0

I have used every DOS version too. I'm just nostalgic like that.

Oldest Operating System on a Physical Computer: Windows 95
Oldest Operating System on a Virtual Computer: Windows 3.0

i only reached the Win2k era

This is my first post, as well.

I would say the oldest Microsoft OS I've ever used on a physical machine was MS-DOS 3.3. The earliest version of Windows I used was 3.1.

I remember the Windows 95 launch very well. I started using Win95 on Thursday, August 24, 1995 - the day it was released.

On various emulators, I've played around practically every version of DOS and Windows, and quite a few versions of the Mac OS, as well.

I used to have a Pentium/120 with Windows 95 (4.00.950). Windows/286 and even Windows 3.0 ran in real mode. That was pretty neat.

As for the earliest non-Microsoft OS I've used on a physical machine ... Apple DOS on an Apple II. I don't remember the version, but I'm pretty sure it was older than MS-DOS 3.3.

At any rate, I'm glad to be on the board!

The oldest OS I have used on a real machine would have to be Windows ME (I was so glad to upgrade to XP!), the oldest one I've used in a Virtual Machine would have to be Windows 3.1

Oldest system on a physical machine was: MS-DOS 5.0
Oldest runned in a VM: MS-DOS 2.03

the oldest, eh?
On real hardware:Windows 98(i think its First Edition)
On VM:MS-DOS 6.22
ahhh, the good old days....

+1 for Windows 3.1

it was the newest out when my family first got a computer... man that makes me feel old.

The oldest I have owned is MS DOS 5.0 Russian on 5.25 inch floppies and Windows 3.0 English on 5.25 inch floppies.
The oldest I have used is MS DOS 4.x Russian and Windows 2.x (I think 2.1) Russian.

Everyone's old, haha. I was first introduced to Windows 95, and still today I wish I could find the same "Snake" game that was on there. That old game is still the best snake game for me, XD. Those hewlett packard days.

Oldest on a physical computer that i've used would be 95, I think. The first computer I remember having had windows 95 on it, but I don't remember much about it. Oldest i've used on a vm would be 95 also. I don't know how to install older versions...

Windows 3.11 For Workgroups on Real Machine, Windows 2.01 on VMWare

On a real Machine: MS-DOS 3.2 that we had cira 1988
Virtual Machine/Emu: MS-DOS 1.25 MBC-550 using MESS

My first computer had Windows 95 on it, with Office 95 AFAICR (yeah! That's what you call an acronym )
Its keyboard had one of these "big PS/2" / DIN - connectors and I'd guess a serial mouse. That must have been like 1999.

As far as VMs go, I'd say PC DOS 1.25.

PC-DOS 1.25? you mean MS-DOS 1.25 (which OEM version?)

Our elementary school had computers running windows 3.something. I remember playing old dos games like word and math rescue and high tech new windows games like sim farm!
I have used physical computers with every Windows os from 3.x up (although not the pre-xp nt line)
I have, like many others, played around with the vast majority of microsoft OSes in virtual machines.

me just windows 95 then a few month windows 98 (year 4)