Objectives: Periurethral masses are an uncommon but challenging diagnosis, with up to ten different etiologies. The list includes: urethral diverticulum, leiomyoma, vaginal wall cyst, Skene’s gland cyst, Skene’s gland abscess, urethral prolapse, urethral caruncle, Gartner’s duct cyst, ectopic ureterocele, and malignancies. There is limited literature addressing the widespread scope of diagnoses in periurethral masses. While urethral diverticula is the most common diagnosis, other pathology can mimic their presentation posing both a diagnostic and therapeutic challenge. Our primary objective of this study was to review the presentation, evaluation, diagnosis, surgical management and outcomes of periurethral masses in women. Materials and Methods: Retrospective chart review was performed of 59 patients over a twelve year period from urology and urogynecology departments at a single academic institution. Demographic, clinical, and surgical data were collected and presented as descriptive statistics. Results: Fifty-nine patients were evaluated for symptomatic periurethral masses with a mean age of 46 years (range = 22-73). The most common presenting symptoms include a palpable mass in 54 (92%), pain 38 (64%), urinary tract infections 27 (46%), urinary incontinence 27 (46%), and frequency 21 (36%). MRI was utilized in 48 of the 59 patients (81%). Cystoscopy was performed on all patients and urethral defects were visualized in only 28 (47%) of the cases. Final diagnosis revealed that 38 (64%) of the periurethral masses were diverticula, with 2 (5%) associated with adenocarcinoma and 4 (11%) associated with previous bulking agents. The remaining periurethral masses were: 7 (12%) Skene’s duct cysts/abscess, 3 (5%) Gartner’s duct cysts, 2 (3%) vaginal wall cysts, 2 (3%) bulking agents, 2 (3%) urethral polyps, 1 (2%) leiomyoma, 1 (2%) angiomyofibroblastoma, and remaining three including redundant vaginal mucosa, suture abscess, and encapsulated mesh remnant. Fifty-seven of the patients underwent surgical excision and 2 elected observations. One concomitant sling was performed with excision and Martius flap was used in 2 patients with circumferential diverticula identified on MRI. Of the patients surgically managed, 4 (7%) had demonstrable SUI and 7 (12%) had lower urinary tract symptoms postoperatively. Of the 38 urethral diverticulum, 6 (16%) had recurrence of a periurethral mass. Overall, 46 (78%) reported resolutions of symptoms after excision. Conclusion: While urethral diverticula most commonly present as a periurethral mass, other pathology can mimic the presentation and a thorough investigation is necessary for correct diagnosis. MRI is most effective in determining the size and location of the periurethral mass. Surgical excision provides reasonable anatomic and functional outcomes for a symptomatic patient. DISCLOSURE OF RELEVANT FINANCIAL RELATIONSHIPS: