Hydraulic models of sewer systems are commonly used to predict the risk of urban flooding. However, suitable calibration datasets in flood conditions are scarce. The quantification of energy losses within manhole structures is a current source of uncertainty within such models. To address this gap, a scaled physical manhole model is used to quantify hydraulic energy losses during surcharging and non-surcharging conditions. Two different novel configurations were tested; (1) With and without the presence of a manhole lid; (2) With and without the presence of a shallow flow on the surface. Results showed that total head losses were found to increase in surcharging conditions. The presence of the lid also marginally increased total head losses. The datasets are used to assess the performance of a numerical urban flood model (SIPSON) and comparisons highlighted that SIPSON tends to overestimate energy losses in surcharging conditions.