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Fight on a dense forest. They start 500 yards apart.

Close actually. Terrain wise, Shino has an advantage. But he would need to get to her to really do much and she'd fight at a distance. She's not stupid either so it may be harder to trick her. Temari has her summon that packs a ton of power behind it. But Shino could end it a lot more quickly with his bugs. Not sure who'd win.

Temari blows him away.

pretty tough to tell. on one hand Shino can send out his bugs and leech her chakra assuming he can get them to hide and jump her, but Temari has that summoning jutsu that can level a good part of a forest and if she pulls that off then Shino isn't going to win.

it's all a matter of whether or not Shino can get to her before Temari pulls out a big time jutsu.

Shino will win here. Temari wouldn't know that the insects have already got into her. (through the ground)

If she doesn't suspect that'll happen and change her position occasionally. Temari's a pretty good tactician.