Flooding may damage important transportation infrastructures, such as roads, railways and bridges, which need to be well planned and designed to be able to withstand current and possible future climate-driven increases in flood frequencies and magnitudes. This study develops a novel approach to predictive statistical modelling of the probability of flooding at major road-stream intersection sites, where water, sediment and debris can accumulate and cause failure of drainage facilities and associated road damages. Two areas in south-west Sweden, affected by severe floods in August 2014, are used in representative case studies for this development. A set of physical catchment-descriptors (PCDs), characterizing key aspects of topography, morphology, soil type, land use, hydrology (precipitation and soil moisture) and sediment connectivity in the water-and sediment-contributing catchments, are used for the predictive flood modelling. A main novel contribution to such modelling is to integrate the spatiotemporal characteristics of remotely-sensed soil moisture in indices of sediment connectivity (IC), thereby also allowing for investigation of the role of soil moisture in the flood probability for different road-stream intersections. The results suggest five categories of PCDs as especially important for flood probability quantification and identification of particularly flood-prone intersections along roads (railways, etc.) These include: channel slope at the road-stream intersection and average elevation, soil properties (mainly percentage of till), land use cover (mainly percentage of urban areas), and a sediment connectivity index that considers soil moisture in addition to morphology over the catchment.