I tried SimpleOCR with Crossover Mac Public Beta and it works fine so far.
I treated it as an unsupported program and told Crossover Mac to make the bottle for the SimpleOCR installer.
It worked well although Crossover didn't know when the installer was finished. I had to tell it to finish the installation and Crossover went ahead and made a Windows "reboot" although the SimpleOCR program had already started and was running just fine without the "reboot".
As far as SimpleOCR goes, there are improvements that could be made (like better rotation support and such) but that's that software maker's issue not Crossover's
The only real problem I encountered was the SimpleORC Help program appeared to be functional but only able to show one help page about a subject I wasn't interested in.
I don't know if this is a SOCR problem or a Crossover problem but I don't have a Windows machine to make the comparison.
Otherwise, as far as I'm concerned, both programs work. The OCR program reads image files and turns them into text as best it can. Crossover makes it possible on a Mac.