Deep infiltrative endometriosis of the anterior compartment is an uncommon but clinically significant form of endometriosis, affecting approximately 6% of cases. This chapter explores endometriosis in the anterocentral compartment, focusing on its involvement of the urinary bladder and round ligament. Bladder endometriosis occurs in less than 1% of all patients with endometriosis, where endometrium-like tissues infiltrate the bladder’s muscularis layer in an outside-in pattern, typically originating at the serosal surface. This condition frequently occurs in patients with a prior history of cesarean delivery, coexists with other pelvic lesions, and may present with symptoms such as dysuria and hematuria. Imaging plays a pivotal role in diagnosis and surgical planning, with transvaginal ultrasonography (TVUS) and magnetic resonance imaging (MRI) serving as essential diagnostic tools, offering high specificity for lesion detection and mapping. On ultrasound, bladder lesions appear as hypoechoic lesions with stellate margins and can contain hyperechoic foci. MRI shows these lesions as T1 and T2 hypointense lesions, which may contain T1 and T2 hyperintense foci. Adherence to adjacent structures can be present with scarring. Round ligament endometriosis is a rare manifestation, involving both intra- and extra-pelvic portions, each characterized by distinct clinical presentations, imaging findings, and surgical implications. Accurate imaging assessment is crucial for guiding surgical approaches and optimizing treatment outcomes. This chapter provides a comprehensive overview of imaging protocols, diagnostic characteristics, and surgical considerations for managing endometriosis involving the bladder and round ligament, emphasizing the importance of precise evaluation for effective treatment.