In cities, the existence of impervious structures, such as road pavements, parking lots, footpaths, sidewalks, and roofs, can limit the magnitude of rainfall infiltration greatly. Stormwater run-off in storm sewer often dominates, which can cause problems of urban flooding easily during heave rainfalls. In rain and sewage diversion, perforated storm sewer is proposed to enable the occurrence of stormwater infiltration into the ground, which can change the prolonged drought-like condition. Model-scale laboratory tests are conducted to assess the infiltration process of water through drainage holes around the sewer circumference. The experimental data are also used to calibrate a numerical model, after which numerical parametric analysis is carried out. It is found that the feature of drainage holes only influences the wetting front in the initial stage of infiltration. In the end, the egg-shaped contour of wetting front with greater influencing zone below the sewer is obtained. The cumulative infiltration with time can be described by an infiltration model, which is positively correlated with the diameter and the number of drainage holes. The optimal opening ratio is recommended as 0.25%, which can provide the most effective drainage capacity.