Team two wins. Location is a dense forest, and Team 8 flourishes tremendously in this location; no idea why I'm seeing Rock Lee solos, smh. The poor guy would get destroyed in this environment.
The only one capable of properly locating and combating team 8 in this location, is Neji. However, even then, he'll have a very hard time given the Insect Jammer technique and bunshins. Meanwhile, Team 8 can freely utilize the location to there advantage and deploy ambushes. Shino's chakra absorbing insects pestering Rock Lee and Neji, while Kiba's 2 or 3 headed wolf technique appearing out of nowhere would be fearsome, in addition to Hinata for added pressure. Shit, I'm inclined to say Kiba and Shino take this, even without her. Lastly, an insect bunshin could potentially wreak havoc for Rock Lee. If he punches through one, they'll just disperse all over him and proceed to restrain and absorb his chakra. I don't know if he'd be able to enter his gates if this would ever occur.
Kiba and Shino take it, medium-high difficulty imo.