Suggested by Anonymous Shikamaru may be a master strategist but there definitely does come a point where it just doesn’t help a whole lot. Isshiki’s just way too powerful of a fighter for this to even matter in the end. Shikamaru’s shadows likely wouldn’t be strong enough to hold him either which puts the guy at even more of a disadvantage. Isshiki Otsutsuki wins.
Suggested by Sonic This is a pretty close fight. Shikamaru has really mastered his Shadow possession jutsu and various other versions where they can actively attack an opponent. At the same time, Sai’s Taijutsu is easily superior and he can create a ton of animals through his ink to keep Shikamaru busy. I see this being a very strategic battle but ultimately I think Sai will pull ahead. Taijutsu is very important in a battle like this where both ninjutsu skills are around equal. Shikamaru would be able to win with prep time but in a straight up fight I’d say it’s his narrow loss. Sai wins.
Captain Kirk may be pretty smart when it comes to battle tactics, but even he would likely admit that Shikamaru is superior in this aspect. Shikamaru’s ninjutsu aren’t quite as flashy as Naruto’s or Sasuke’s, but he knows how to use his abilities in the most efficient way possible. I’m afraid that Captain Kirk is simply outmatched here. Shikamaru wins.
Shikamaru is a very smart fighter and he has some decent offensive capabilities as well thanks to his Shadow Stitching jutsu. His big weakness is hand to hand combat and that’s an area where Joseph Joestar excels. Shikamaru can keep him at bay for a while, but Joseph will eventually break through his defenses. That will be the end of the match since Joseph’s physical abilities are far too great for Shikamaru to last against for very long. Joseph Joestar wins.
Both of these fighters are facing their first battle! Shikamaru is definitely the smarter fighter of the group, but he’s a lot less of a fighter. Lavi showed some intense fighting abilities when he fought Allen. I think he could outfight Shikamaru and stop him from thinking a plan to win. Lavi wins.