Wine - Open Source Software for running Windows applications on other operating systems.
CSE Classroom Manager - Technology for Education
CodeWeavers CrossOver - Don't buy a Windows license, don't reboot and don't use a Virtual Machine. Try a free trial of CrossOver to run your Windows software on Mac, Linux and Chrome OS.
NetSupport School - NetSupport School supports a teacher with a wealth of dedicated assessment, monitoring, collaboration and control features.
Darling - Run macOS applications on Linux
Class Charts - Class Charts is super fast behaviour management software, creating school seating plans in seconds.