This one seems a lot more even in power than Shikamaru vs. Wrath, plus they have similar abilities. So, the two fight in some flat terrain, plains or something.
His control over shadows makes Shikamaru's look pitiful, able to control them over a country-wide area in suitable conditions, and they are able to cut through steel easily.
Their shadow controls are very different, all in all, in a way that favors Pride. Shikamaru's shadows mostly remain as flat shadows, and their primary usage is snaring and manipulating people.
Pride's are basically giant blades/mouths/eyes that happen to be made of shadow.
Shikamaru might be able to get a few 'kills' with explosive tags or strait-up knives or shadow-sewing, but shadow-grap does nothing at all to Pride's main body (well, it makes the main body not move, but who cares? It doesn't have to to attack) and Pride's shadows are way higher offense, so he's not going down.
Hm... unless Shikamaru can manipulate his shadow to cover Pride entirely, thus preventing the manifestation of Pride's shadows... but, no. He wouldn't be able to finish the job like that and it'd be very temporary at best.
Shikamaru's pretty screwed. Even with clever tactics he can't hope to get enough kills.