>>435481841. Sabrina
2. Clair, especially if you don't have an ice type. And considering all the ice types come in at a point where they're severely underleveled compared to your party, you might not be planning on picking one up.
3. Norman can be difficult if you're unprepared.
4. Fantina
5. Elesa in BW, especially if not packing a ground type, and I honestly find Cheren the hardest in B2W2 because your team might just not be developed enough at that point depending on how you're planning on filling it out.
6. No one gave me any trouble at all, but I guess Grant? If you're not packing the right Pokémon he can be hard, but not especially so.
7. Totem Wishiwashi in SM, and I found Totem Marowak in USUM to be hard.
8. Just like in Gen 6 nothing really challenged me, but I'd say I had the most trouble with Kabu due to poor match ups against my current team at the time.