Hi Paul,
There is a manual method of transferring your Outlook data from Mac to Windows, but the method is a bit complicated and very tedious, as you have mentioned that the size of the OLM file is 39 GB. So it would take you forever to go through with the process.
I would recommend you to use third party conversion tools to convert that OLM file into a PST file so that Windows Outlook is able to read that file. There are many of such tools available in the market you can choose one as per your own needs.
But still even after conversion your PST file size should not be that much, as PST files of huge size tend to get corrupted, so delete the unnecessary data which you don't need to avoid such issues keep the file size less than 20GB and archive the rest of the data.
But if you still would like to go with the manual procedure, i would advise you to transfer only necessary data.
Follow the link to the blog to learn the manual conversion technique: http://wordpress.semnaitik.com/2014/02/13/convert-olm-to-pst/