I would like to suggest you can use Vartika OLM to PST Converter software to convert all OLM file to PST format, The Software is a perfect solution for move Mac OLM to Windows PST Format. The software supports all versions of MS Outlook to Windows. you can also try the free demo versions of this Software.
Know more info- https://www.perfectdatarecovery.com/en/store/12/vartika-olm-to-pst-converter.html
If you would like to move Mac OLM emails to Outlook PST files, you can use the OLM to PST Converter Tool, which is one of the greatest reliable programs available. It has larger features that make it easy for users to switch their OLM emails to PST. This utility can bulk convert numerous OLM files to PST without moving the order, styles, email headers, or email formatting of OLM emails.
Find more information: https://www.gaintools.com/olm/pst/
Copy Messages from Outlook Mac to Windows
You can export emails from Outlook for Mac to EML format and then import EML file to Outlook on Windows. For this, you need to drag and drop the emails from the mailbox folders in Mac Outlook to a local folder on the system storage media. The steps are as follows,
Open Outlook on Mac and select the messages that you want to convert to PST format.
Create a new folder on Desktop and drag ‘n’ drop selected messages from Mac Outlook to this folder on the Desktop.
The messages are saved in EML format. Copy these mails to an external drive and then connect this drive to your Windows PC.
Open Outlook on Windows and create a new folder in Outlook mailbox.
Drag ‘n’ drop the messages in EML format from the external drive to the new folder that you created in Outlook for Windows.
After this, open Import/Export Wizard in Outlook for Windows and export all the folders that contain copied EML emails to PST format.