Aim: To see challenging presentations of pyometra in different age groups. Background: The collection of purulent substances in the uterine cavity is termed pyometra. It has been an entity with myriads of presentations, ranging from amenorrhea to vaginal discharge, to acute catastrophe like spontaneous perforation leading to pyoperitonitis and further increase in morbidity and mortality. It is an entity of rare occurrence and constitutes only 0.01–1.5% of gynecological cases. It assumes its importance in postmenopausal females as associated malignancy is found in as high as 22.2% of cases. The main pathological trigger is impaired drainage of shed endometrial lining due to cervical canal stenosis. Case description: We present four cases in this case series. One case presented as a spontaneous uterine rupture with pyoperitoneum, and an emergency laparotomy was performed for this patient with a hysterectomy and peritoneal lavage. Another patient with persistent vaginal discharge was diagnosed with genital TB, and pyometra was drained with endometrial sampling, and the patient was started on anti tubercular therapy (ATT). The third case of patient with persistent blood-mixed discharge had low grade squamous intraepithelial lesion (LSIL) and she was managed by hysteroscopy-guided endometrial biopsy and colposcopy followed by laparoscopic hysterectomy. The last and very interesting case was secondary amenorrhea with grade II Asherman's syndrome with pyometra. Hysteroscopic adhesiolysis was done followed by cyclic estrogen and progestin therapy. Conclusion: Pyoperitoneum presents in a wide spectrum of age groups, albeit with a rare frequency. Owing to its decreased exhibit in literature, the diagnosis is usually delayed. Complicated pyoperitoneum leads to considerable morbidity and even mortality. In postmenopausal females, atrophic endometrium is the most common cause, but in younger patients, the etiological array is quite varied. Timely diagnosis and personalized treatment approach improve outcomes in these patients. Clinical significance: In clinical practice, whenever we come across a case of pyometra, we not only think about tuberculosis but also other such modalities like those mentioned in this case series should be kept in mind. Another word that is to be given through this article is that the differential of pyometra should not be restricted to postmenopausal age group. It should be thought of in the reproductive age group as well.