Pumblechook, Pip's uncle, arranged for Pip's first meeting as a boy with Miss Havisham. Of course, Pip and his sister's hope was that a relationship with Miss Havisham would lead to her sponsoring his training as a gentleman. One thing that Pumblechook does not dwell on, however, is that Pip is not the only boy who sometimes goes to Miss Havisham's. So, Pip's uncle really has no reason to gloat on his "successful" match.
In Chapter 28 when Pip learns from Mr. Jaggers that he has a mysterious benefactor who wishes to remain anonymous but who wants to sponsor Pip's becoming a gentleman, Pip and Pumblechook both assume that Miss Havisham is the benefactress. So, Pumblechook thinks that he deserves Pip's gratitude and recognition because he originally set up the meeting between Pip and Miss Havisham. Of course, the reader discovers later that Pip has no reason to thank Pumblechook since Miss H is not the unknown sponsor.