Shino, high - extreme diff.

Can’t trap bugs in shadow possession can you I wonder? Probably shino low diff. Shino can be a close and long range fighter.

He can just spread his bugs out so it would be more difficult for Shikamaru to trap them all individually. There was a reddit post about this matchup and some user said "Shadow possession was, according to the databooks, invented to capture deer. It 100% works on animals and I think that includes bugs."

It’s like they don’t know the difference between a large mammal that can easily be spotted and tiny creatures that are harder to track

Since this is when they’re young I’d have to say Shino. They were both smart even as kids and would try to outsmart each other. For Shikamaru he’d want to instantly close the gap and make it hand-to-hand combat. He’d want to aggro Shino and not give him time to set up or time to think. Shikamaru would want to force Shino onto the defensive at least until he was able to distract him long enough to use shadow possession on him. That is- Shadow possession on Shino before he could use his bugs. But Shikamaru getting close would give Shino the opportunity to plant on him and do him like Kankuro. If Shino were to plant one on Shikamaru then Shikamaru could possess his shadow all he wanted but after awhile Shino’s bugs would do him in. Shikamaru’s only chance would be to try to beat him out the ring or get him unconscious before that happened. I don’t think Shikamaru would have enough time to take hold of all the bugs, if he focused on that then Shino would be able to fight him. It’s Shikamaru vs Shino and all his bugs and he could use his bugs as a defense or offense as well as still be able to fight hand to hand even tho he wouldn’t have to do much of that.