Introduction: Adenomyosis is a benign gynecological condition that predominantly affects women in the late reproductive age. It is a real challenge in healthcare with prevalence ranging from 5 to 70%. It is characterized by uterine enlargement caused by ectopic rests of the endometrium within the myometrium. It is mainly associated with abnormal menstrual bleeding and severe dysmenorrhea. But now it can be done by advanced imaging modalities like transvaginal ultrasound (USG) and magnetic resonance imaging (MRI). Materials and methods: A prospective longitudinal study was conducted from November 1, 2018 to January 31, 2020 on subjects with complaints of abnormal uterine bleeding and or with dysmenorrhea in the department of obstetrics and gynecology (OBG) of a tertiary care hospital and medical institution. Various medical and surgical treatments were offered on merit depending on age group and clinical symptomatology. The subjects were followed up for a minimum period of six months thereafter. Results: It was found that out of the patients who had visual analog scale (VAS) score less than 7, 22.58% had adenomyosis with normal uterus while 12.90% had bulky uterus with adenomyosis on ultrasound. Of the patients who had VAS score more than or equal to 7, 9.68% had adenomyosis with normal uterus while 54.84% had bulky uterus with adenomyosis. MRI supplemented the ultrasound findings and was found useful in the confirmation of adenomyosis. Conclusion: The clinical diagnosis of adenomyosis has been called enigmatic largely because there are no pathognomonic symptoms of this disease. Ultrasound and MRI are found to be highly useful in supplementing the correct diagnosis of adenomyosis.