Build libdvdcss 1.4.0 for Windows 64-bit
The latest version of libdvdcss-2.dll for Windows (64-bit) available for download is 1.2.12 (released in 2012). Since the source for 1.4.0 (released in 2015) is available, this tutorial will walk you through the process of compiling it on Xubuntu. After you're done, you can move it to a Windows machine for use.
Step 1 - Install the Mingw-w64 Toolchain
Install the necessary tools to build the dvd access library.
Step 2 - Download and Extract the libdvdcss Source
Download the source code for the latest version of libdvdcss from the VLC website.
Step 3 - Compile Source
Tell configure to use the compiler for Windows 64-bit and run make to build the binary. It may give you a few warnings, but it should successfully build the libdvdcss-2.dll in a (potentially hidden) .libs folder.