Can I get sound from 2 different apps on the same computer to come out of 2 different speakers?

I have my speakers and sub woofer plugged into the ports on the back of the computer, and my headphone/mic plugged into the ports on the front of the computer. Is it possible to get sounds from skype to come through my headphones, but the sound/music from Windows Media Player to play through my speakers and sub woofer? I’ve done some searching and cant find anything, you’re my last resort, Fluther!