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Prostatic adenocarcinoma and urothelial carcinoma are common tumours seen in elderly patients. They both act as a close differential diagnosis for each other clinically as well as histologically. Various morphological patterns have been described in prostatic adenocarcinomas. However, pseudopapillary pattern was not described until recently a paper which described seven such cases. These tumours mimic urothelial carcinoma as the papillary pattern is usually seen in urothelial carcinoma and may act as a pitfall for the diagnosing pathologists. As both the tumours are treated with different therapeutic protocol it is necessary to differentiate the two and hence the pathologist should be aware of this morphological variant of prostatic carcinoma. Critical histological review and immunohistochemical examination is helpful to make the diagnosis. Here we discuss one such case of pseudopapillary prostatic adenocarcinoma mimicking urothelial carcinoma with a brief review of histological and immunohistochemical examination useful to distinguish the two tumours.