Urachal cysts are one of a spectrum of urachal abnormalities that occur following failure of regression of the allantois and presumptive bladder between 4 weeks and 6 weeks of gestation. Infection is the most common complication of this rare congenital anomaly. The nonspecific presentation may mimic other pathological processes, underlining their clinical and radiological significance. Imaging investigations typically include US and CT, both of which are limited in their ability to characterize lesions. We report the case of a 5-year-old presenting with macroscopic haematuria in whom diffusion-weighted MRI (DWI) suggested the diagnosis of an infected urachal cyst, which was confirmed surgically. We discuss the radiological findings in multiple imaging modalities and present the application of DWI in this context as a means of improving the radiological diagnostic yield.