Hello, I'm wondering if it's possible to run Winbox and automatically have it prefill the address field and password, using the CMD prompt in Windows.

We use a database software to keep track of devices, and we would like to be able to start the session, and automatically have Winbox open up with as much information as possible. Thanks.

Yes. You can pass them as command line arguments :

winbox.exe <ip> <username> <password>