Bit of a Noob moment coming. I currently have my speakers plugged into my mother board via the rear port. I would like it so that when I plug my headset into the front audio port on my case it switches the audio from the speakers to just the headset. I honestly have no idea how to do this, and assumed it would be the standard thing to happen.
It is the standard thing to happen. If you're using AC'97 audio, I'm pretty sure it's accomplished through the physical switch built into most 1/8" audio jacks, in which case if it's not working it seems likely your case doesn't support the feature. If you're using Intel HD Audio, it's a software function, and you should make sure your drivers are installed correctly. I use HD Audio, and when I plug my headphones in, my audio driver brings up a dialog box asking me to confirm what I've plugged in. You can also set the software to behave differently, so it's possible you're using this system and long ago changed the settings around in an unfortunate way. Reinstalling the driver should fix it, although you're quite welcome to crawl around in the settings panel first if you find that more appealing.