How to install Championship Manager 01/02 on MacOS Catalina
With the installation of MacOS Catalina 32bit application support is no more. PlayOnMac, Wine and Crossover all no longer function. Read on to find out how we got Championship Manager 01/02 working, all over again!
A couple of years ago we worked out how to get CM0102 working on Mac using PlayOnMac and Wine, with a little manual tinkering. This was an excellent solution as it was lean, fast, and importantly, free. With the advent of MacOS Catalina this solution stopped working, as did the commercial WINE wrapper Crossover. WINE is unlikely to be ready for full 64 bit support for quite sometime, Crossover may have a workaround in early 2020.
Here at MacRetro retro gaming is pretty much the only kind of gaming that we do, and although we do have a linux gaming machine in the house, playing on the tower both defeats the purpose of this domain, and doesn't travel well either!
So we looked at the horizon, decided that there would not be a viable solution any time soon, so we came up with a new one. First we tried to run PlayOnMac inside a Linux Mint Virtual Machine. Not only did CM0102 not work, neither did anything else we tried to run.
Next we decided to try to run games natively inside a Windows XP virtual machine on Mac, pretty much every game other than CM0102 worked - until we realised why CM0102 was not loading, and that it was something that we'd had to fix when running XP all those years ago too!
We looked at two different pieces of software to run this in - we looked at VMware and at Parallels. We opted for the latter mainly because it has a nice and easy GUI to walk you through VM setup. We are using "Parallels Desktop Lite" which you can purchase through the App Store. It is more expensive than buying and renewing Parallels Destop Pro directly, but it does allow Parallels to be used on all of the machines in your apple account. If that was not important to us (it is), we'd have bought the Pro application instead. More detail on this another day.
So installing CM0102 in a Windows XP VM is pretty much the same as installing CM0102 on a windows XP machine way back then.
- Attach your CM0102.iso to the virtual CD ROM drive available in Parallels:

- Select your installation language:

- Watch your game install

- Right Click (or centre click) on CM0102 icon on desktop, and load the properties menu.

- Select the "Compatibility" tab in the dialogue box that loads:

- CM0102 will not load in Windows XP - set compatibility mode to Windows 95

- Play CM0102 on your MacOS Catalina Machine!

This is not the cheapest way of playing old windows games on Mac, and it is certainly not free. It is however very robust, and opens the door to other possibilities - the Tapanified CM0102 updates will work in this Windows XP VM, they did not work in the PlayOnMac solution. If you have not upgraded to macOS Catalina yet, you do have the option of remaining with your current PlayOnMac setup - but you will need to turn automatic upgrades off, and will not be able to upgrade your MacOS installation without breaking your setup.
If you are worried about whether this solution will work with your game, CM0102 or otherwise, then Parallels offer a 14 day trial of their software with no card details upfront - so give it a go. Oh, and in the interests of transparency, we have no relationship whatsoever, affiliate or otherwise with Parallels - and sadly we earn no money at all if you buy their software too. We're just really excited about the Windows XP virtual machines that we've built using their kit!
Game On!!!!!