Contest #6 was won by the former Wisconsin State Debate Champion, the Honorable Doctor Benjamin Bayer PhD. The answer is the Dutch/Belgian enclaves/exclaves of Baarle-Hertog and Baarle-Nassau.
Seriously, guys. I thought this one would be much more difficult. I really need to think of something a bit harder.
Co-champion. We all know Nate carried me. 😉