vDos (vdos.info) was a huge life saver for this application. It's similar to DOSBox, but more tailored to business applications. The big issue was always to find compatible printers for the old application, vDOS includes some emulation to print to any Windows printer.
There might be free alternatives to vDos, but it worked very well and is reasonably priced.
PS: we also tried to recompile the Clipper source code with Harbour to modern targets. It looked very promising, but they were extremely happy with the vDos solution, which only took 2 hours to deploy.