Introduction. Masses arising from structures adjacent to the female urethra can cause obstructive urinary symptoms. Subpubic cartilaginous pseudocyst is a rare degenerative lesion of pubic symphysis that may cause these symptoms. Materials and Methods. A 61-year- and 57-year-old women presented with symptoms of difficult micturition and dyspareunia. Physical examination revealed a painless smooth, rounded, firm, and cystic mass, at the anterior vaginal wall of about 4 cm width. The mass caused inward deviation of the external urethral meatus. Cystoscopy and MRI were done. Results. Cystoscopy of case 1 (61 y) demonstrated anterior external urethral compression with normal urethral mucosa. Cystoscopy was not possible in case 2 (57 y) because the urethra could not be entered under local anesthesia. MRI showed almost the same findings in both cases: midline, rounded, and cystic mass ~3 × 3 × 4 cm, anterosuperior to the urethra, and posteroinferior to the pubic symphysis, with normal features of the urinary bladder. Open surgical excision of theses lesions was performed in both patients. Histopathologic assessment of the specimen obtained from both patients showed degenerated hyaline with areas of fibrinous and mucoid degeneration, a picture suggestive of cartilaginous subpubic pseudocyst. After 11-month and 4-month followup of patients numbers 1 and 2, respectively, there is no evidence of local recurrence of the lesion, either clinically or radiologically and both patients void empty. Conclusions. Subpubic cartilaginous pseudocysts are rare benign lesions with only 13 cases were reported in the literature. Patients present with a spectrum of gynecological and/or urological manifestations. Sizable lesions severely compressing the urethra need surgical excision to restore the voiding function.