Middendorp will have his first encounter against Mokwena since the latter took over the reigns at Pirates in August, upon the departure of Milutin Sredojevic.
The two Soweto giants meet in a Telkom Knockout quarterfinal clash at a sold-out Moses Mabhida Stadium in Durban on Saturday afternoon (15h00).
The 32-year-old Bucs mentor has endured a rude awakening to life as a top flight manager, after having previously only served as a first team assistant and a youth team coach.
The 61-year-old Amakhosi intructor has withheld his early assesment of his counterpart, insisting that he needs more time to suss out his progress as a coach.
"It's a question I basically will not answer because I have not worked with him; because I haven't seen him being responsible for a team over a certain period," said Middendorp.
"I think it's good that the clubs have the idea to bring [young] coaches in with a new flair, a new idea - no problem at all, otherwise I can't really say too much about [how he's doing]. It's a certain period he's in, the changes are there."
Middendorp also picked out some wise words for Mokwena, who has repeatedly admitted to taking inspiration from the likes of Jurgen Klopp, Pep Guardiola and Jose Mourinho, instructing him to walk his own path rather than copying and pasting others' philosophies.
"[He is] following big philosophies – it's fine, it's okay, but this is what you find out over the years: Build up your own reputation," he added.