Soil surface roughness not only delays overland flow generation but also strongly affects the spatial distribution and concentration of overland flow. Previous studies generally aimed at predicting the delay in overland flow generation by means of a single parameter characterizing soil roughness. However, little work has been done to find a link between soil roughness and overland flow dynamics. This is made difficult because soil roughness and hence overland flow characteristics evolve differently depending on whether diffuse or concentrated erosion dominates. The present study examined whether the concept of connectivity can be used to link roughness characteristics to overland flow dynamics. For this purpose, soil roughness of three 30-m2 tilled plots exposed to natural rainfall was monitored for two years. Soil micro-topography was characterized by means of photogrammetry on a monthly basis. Soil roughness was characterized by the variogram, the surface stream network was characterized by network-based indices and overland flow connectivity was characterized by Relative Surface Connection function (RSCf) functional connectivity indicator. Overland flow hydrographs were generated by means of a physically-based overland flow model based on 1-cm resolution digital elevation models. The development of eroded flow paths at the soil surface not only reduced the delay in overland flow generation but also resulted in a higher continuity of high flow velocity paths, an increase in erosive energy and a higher rate of increase of the overland flow hydrograph. Overland flow dynamics were found to be highly correlated to the RSCf characteristic points. By providing information regarding overland flow dynamics, the RSCf may thus serve as a quantitative link between soil roughness and overland flow generation in order to improve the overland flow hydrograph prediction.