With intel, it would be a good match then, nothing one-sided
I hated their fight because it didn't show what they are truly capable of.
I think what the Novel says about Temari helping Shikamaru and the other Nara clansmen create a technique that uses light to expand the shadow was true, though I'm not 100% sure because I don't speak Japanese. I just remember Shikamaru looking at Naruto and exchanging a few words before he joined up with his wife and daughter (this was before Boruto cheated).
In the battle itself you truly see them both shine, and it's heart pounding for the only minute it has. In the beginning of the fight you mostly have Boruto coming in close, and coming out. You see him using the Hyuuga Taijutsu as he tries to attack directly but he moves out every other second to stay away from the shadow possession jutsu.
In between Boruto had chances where he came in close, jumped through but Shikidai caught him in the shadow possession. I believe he tricked him with a shadow clone and came running behind him again, or he broke out of it using conventional means.
A few seconds in you have them both going back and forth, this time Boruto is using the shadow clone jutsu (he would wait for Shikidai's shadow possession jutsu to come in close, and then he would create a shadow clone jutsu to trick him into tagging the clone, and then he would jump off the clone jutsu and come in close).
The fight ended with Boruto creating a few shadow clones coming at him and Shikidai trapping them all using his super neat technique that expanded.
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Overall I think it's obvious that Shikidai has larger reserves than Shikimaru as his age, most likely due to Temari's side. Boruto is no fool either unlike his father, actually his Zai No Sho (sort of like the Movie Data-Book) called him "smart".
Though I feel like they had more to offer, both being called Prodigies and all. I'm sure Shikidai has more in store outside of shadow possession, I mean Temari is his mother. Same goes for Boruto.
