Noob here, but for what it's worth:
I know that after messing with the Windows settings with no luck, I've discovered that the specific media players have their own set of calibration settings. VLC, for example, has a ton of options for configuring audio output.
Also, in addition to Windows sound settings, look for such things as Realtek audio settings (if that's what you're pushing from) or, if you're going the HDMI route out of a video card, Nvidia or ATI control panel or some such thing(s).