Phoebe vs Grimmjow

Phoebe is a pretty skilled gym leader. She has a solid array of Pokemon at the ready so Grimmjow will have to worry about more than one opponent at a time. Even with that it shouldn’t be a problem for him to win the match though. Grimmjow is an Espada and as such he has access to the Cero blasts. A Cero covers a wide range of territory in each hit so he could hit all of her Pokemon at once and then with quick hand to hand moves knock them out of commission. Grimmjow wins.

Gravity Beetle vs Phoebe

Suggested by Anonymous Phoebe has a good array of Pokemon at her disposal. While her sheer numbers may not be quite as great as other leaders, they certainly still do lead the round to her favor either way. Gravity Beetle’s attacks are meant to keep his opponents pinned but he can’t trap all of them at once. Phoebe’s Pokemon are also pretty powerful in their own right so together they are more than a match for anything Gravity Beetle throws their way. They simply won’t falter here and Gravity Beetle isn’t equipped to take them all down. Phoebe wins.