I'm not a licensing expert, so the answer below is from Vinicius, our marketing PM:
What you see below is not the same product. The first one is the Windows Server Standard license itself. The second one is the Client Access License (CAL) which is needed for every user or device connecting to the Windows Server. The one below is a User CAL, which means that no matter how many devices the user has, he can connect to that WS. A Device CAL, which is not listed there, enables the device to connect to WS, so no matter how many users share the same device.