The test results you have selected are very old and may not represent the current state of Wine.
Selected Test Results (selected in 'Test Results' table below)
In short: the software runs, whereas the installer poses some difficulties.
The CDROM comes with software that works under W9x and above. I configured wine as a W98.
Before the installation, I copied the content of the CDROM into a a folder that I mapped as a drive using winecfg.
I tested the dictionay with wine-0.9.8. I am using this version because this is the one that comes with Gentoo-Linux (AMD64). I can compile and execute newer versions, but I cannot get their fonts to work.
The installer copies its own fonts but makes heavy use of OLE calls. Under wine-0.9.8 the installer exits with an error after displaying a logo. I compiled wine-0.9.14 and run the installer with it. Of course, I could not see the labels or the text I typed, but I had practised the sequence a couple of times with a real windows box before.
I am not sure if the installer really succeeds, because some files must still be copied by hand (ew_lkg.bof, ew_lkg.idx, and ew_lkg.fsi into the home directory or drive C:) and because the dictionay must be manually added ("Datei -> Bücher hinzufügen" and then select (via "Durchsuchen") the only file in the "data" subdirectory.)
What does not
The software includes an option to update the vocabulary. This option uses the internet. To update the product, a registration is needed (Anmeldung zur Wortschatz-Aktualisierung). But the registration is triggered from inside the application. When I click on the button to registrate, nothing happens. I guess the software is looking for IE or the default navigator. I do not have IE (too expensive).
I will try the update-thing using a Windows machine.
What was not tested
Wine version was not the same during install and during run.