Background: Bilateral ureteroceles in adult males are a rare occurrence, made even more so with simultaneous presence of bladder calculi. Management strategies for such patients are not well documented in the literature. We present a rare case of bilateral open ureteroceles with large concomitant bladder calculi to contribute to the paucity of literature on management of such patients. Case Presentation: We present the case of a 35-year-old man whose gross hematuria work-up demonstrated right-sided hydroureteronephrosis in the setting of bilateral ureteroceles and multiple large bladder calculi up to 3.8 cm. Conclusion: Bilateral orthotopic single-system ureteroceles in an adult male are a rare finding especially when intraoperatively found to be open secondary to traumatic effects of large calculi. Ultrasonic and pneumatic lithotripsy is a safe, appropriate, and effective option for bilateral ureteroceles contributing to a large bladder stone burden. Our report contributes to the growing body of literature on orthotopic bilateral single-system ureteroceles in the adult population with concomitant significant stone burden.