I've using Macs ever since my family bought a Mac Plus in 1986. When QEMU came out with the ability to run Mac OS 9-10.4 I knew I wanted to try to run every Mac OS at once. I finally tried it. I had to spread the windows over my 2 monitors to show all the versions. Enjoy!
This doesn't include any developer seeds or betas; just shipped versions. Version numbers taken from https://en.wikipedia.org/wiki/Classic_Mac_OS and https://en.wikipedia.org/wiki/MacOS
Emulator/Virtualizer and OS Versions
Mini vMac 128K
- Macintosh System Software - System 0.97 & Finder 1.0 - Jan 24, 1984 - The first release
- Macintosh System Software 0.1 - System 1.1 & Finder 1.1g - May 5, 1984 - Last System 1.X
Mini vMac 512K
- Macintosh System Software 0.3 - System 2.0 & Finder 4.1 - Apr 1985 - Shut Down and MiniFinder arrive
Mini vMac Plus
- System Software 1.1 - System 3.2 & Finder 5.3 - Jun 1986 - Last System Software 1.X
Mini vMac II
- System Software 2.0.1 - System 4.1 & Finder 5.5 - Mar 2, 1987 - Welcome Mac SE & Mac II, last System Software 2.X
- System Software 5.1 - System 4.3 & Finder 6.0 - Nov 1987 - MultiFinder has arrived, last System Software 5.X
"Wait, what happened to System Software 3 & 4?" There never was any. Apple started to bring the system software version inline with the actual System & Finder versions starting here with System 4 & Finder 6 being averaged, if you will, to 5. From here on they are the same major version number and the System/Finder version numbers will be omitted.
- System Software 6.0.8 - May 13, 1991 - Final version of "System 6", System 7 had been out almost a year at this point.
- System Software 7.0.1 - Oct 1991 - Patched up version of the first version of System 7
Basilisk II - Mac IIci Emulation
- System Software 7.1 - Aug 1992 - Fonts move out of the System into the Fonts folder
- System 7 Pro (7.1.1) - Oct 4 1993 - PowerTalk, QuickDraw GX & QuickTime, Oh My!
SheepShaver - Old World ROM
- System Software 7.5.5 - Sep, 18, 1996 - Final System 7.5, last version that will run on 68000 Macs or Macs that aren't 32-bit clean
- Mac OS 7.6.1 - Apr 7, 1997 - Apple really starts to push calling the system Mac OS (the startup routine said Mac OS starting in 7.5.1) but the About box still says System Software, final System 7.6
- Mac OS 8 - Jul 26, 1997 - I included Mac OS 8.0 because of the failed Copland project that was to be a fully modern Mac OS, but at least we got the Platinum UI, requires 68040 or PowerPC Mac
- Mac OS 8.1 - Jan 19, 1998 - Last version to support 68040 Macs and introduced HFS+ or Mac OS Extended file system
SheepShaver - New World ROM
- Mac OS 8.5.1 - Dec 7, 1998 - Last 8.5.X version, includes major bug fixes for 8.5
- Mac OS 8.6 - May 10, 1999 - First nanokernel Mac OS for multiprocessing goodness
- Mac OS 9.0.4 - Apr 4, 2000 - Last 9.0.X version, last version for "Old World" Macs with no MMU.
QEMU - PowerMac G4
- Mac OS 9.1 - Jan 9, 2001 - Last version to run on any PowerMac
- Mac OS 9.2.2 - Dec 5, 2001 - Last version of Classic Mac OS, requires Mac OS X compatible Mac
- Mac OS X Cheetah 10.0.4 - Jun 21, 2001 - First version of Mac OS X (Non-Server) with updates, "Lickable" Aqua interface, my first PowerMac G4 came with Mac OS 9.1 and Mac OS 10.0.3
- Mac OS X Puma 10.1.5 - Jun 6, 2002 - Distributed for free at Apple Stores and other retail stores (I got mine at CompUSA)
- Mac OS X Jaguar 10.2.8 - Oct 3, 2003 - Quartz Extreme! It seemed that each new version of OS X was getting faster and faster
- Mac OS X Panther 10.3.9 - Apr 15, 2005 - Exposé, FileVault, etc, etc
- Mac OS X Tiger 10.4.11 - Nov 14, 2007 - Last version to run Classic Mac OS software, First version of OS X (10.4.7) to run on Intel Macs
- Mac OS X Leopard 10.5.8 - Aug 5, 2009 - Time Machine, no more Classic and the start of 64-bit support
- Mac OS X Snow Leopard 10.6.8 - Jun 23, 2011 - Goodbye PowerMac support, Hello bug fixes, performance enhancements and eventually the Mac App Store, last version to run PowerPC OS X software via Rosetta
- Mac OS X Lion 10.7.5 - Sep 19, 2012 - No more PowerPC apps or optical disk distribution, download or (eventually) USB flash drive only
- OS X Mountain Lion 10.8.5 - Sep 12, 2013 - Like Lion but more refined, see Snow Leopard, oh yeah and GateKeeper, also it's just OS X now, thanks
- OS X Mavericks 10.9.5 - Aug 7, 2014 - We had cats, but now we have places in California, this one named after a dog; skeuomorphism on the way out
- OS X Yosemite 10.10.5 - Aug 13, 2015 - Dark mode! Well for the menu bar and dock, a flatter, more translucent interface, skeuomorphism gone
- OS X El Capitan 10.11.6 - Jul 18, 2016 - Like Yosemite but more refined, see Snow Leopard and Mountain Lion
- macOS Sierra 10.12.6 - Jul 19, 2017 - Siri, Apple Pay, iCloud desktop & docs etc, and Yay! Mac is back in the name
Native - Not Emulated or Virtualized
- macOS High Sierra 10.13.5 - Jun 1, 2018 - Like Sierra, only Higher; not necessarily a bug fix release but has been a lot more stable with the later updates
Not included but possibly should/could have been:
- Macintosh System Software for Hard Disk 20 - System 2.1 & Finder 5.0 - Last System 2.X and first Finder 5.X, not included because I had a 2.X version already I guess
- System 7.1.2 - System 7.1.2 & Finder 7.1.4 - The first Power Macintosh System software. As far as I know there are no emulators for the very first Nubus Power Macs. You can run 7.1.2 in an emulator if you install the version for Quadra 630. This was convoluted, however, as I had to install 7.1 to a IIci and then upgrade that installation to 7.1.2 and remove a couple of offending extensions. I never could get 7.1.2 to boot an emulated Quadra in Basilisk II.
- Mac OS X Server 1.0 - Does this count? It's Next OpenStep with a Platinum skin. I have often wondered how widespread the use of this software was.