Most likely it is the fact that you're running an old browser on the server and the site doesn't support it. Windows Server is going to be running IE 11 which many sites don't support. It could be related to the site itself using bad paths but you'll see that on other machines as well.
Use your browser's F12 tools to look to see where things are failing. This is likely not an issue you just cannot browse from the server. Browsing from the server is only useful when you're diagnosing site permissions or runtime errors anyway.