Head loss in surcharged four-way junction manholes is a factor that increases damage due to urban inundation; thus, the flow characteristics of such manholes must be analyzed to reduce the head loss. In this study, a physical model was constructed; this model included a manhole and a connection pipe, fabricated on a 1/5 scale by applying sewer facility standards to perform a physical model investigation. Numerical simulations were performed using the Fluent model to derive efficient benching designs that can reduce head loss. Physical model investigations were performed by varying the ratio of the lateral influent flow rate to the effluent flow rate as well as by varying the effluent flow rate and benching designs. The result of physical model investigations showed that the installation of half rectangular benching reduced the head loss coefficients by 7% and 10% on average compared with square and circular manholes, respectively. The installation of full rectangular benching reduced the head loss coefficients by 28% and 17% on average compared with square and circular manholes, respectively. Thus, the benching proposed herein can be installed and used to improve the drainage capacity of urban stormwater conduit facilities.