Primary glandular tumors of the urachus and urinary bladder are an intriguing group of clinically and morphologically diverse neoplasms for which there have been recent refinements in diagnostic subclassification and advances in molecular pathology. In addition, the urachus and urinary bladder may be secondarily involved by tumors with glandular differentiation that demonstrate remarkable morphologic, immunophenotypic, and molecular overlap. Thus, surgical pathologists need to be aware of the broad differential diagnosis of glandular tumors that involve the urachus and urinary bladder and have a practical diagnostic framework to evaluate these lesions in routine clinical practice. In this review, we summarize the salient clinical, morphologic, immunohistochemical, and molecular features of glandular tumors of the urachus and urinary bladder, including mucinous cystic tumors of the urachus, noncystic urachal adenocarcinomas, urothelial carcinomas with glandular or pseudoglandular features, primary urinary bladder adenocarcinomas, and Müllerian-type carcinomas, highlighting the strengths and limitations of various diagnostic features and ancillary tests, as well as the need for close clinical and radiographic correlation.