Agricultural intensification has led to a large increase in drained arable land and pastures worldwide over the last two centuries. The installation of land drains not only affects the water balance of a landscape, but also influences the susceptibility to erosion, nutrient cycling, transport of plant protection products (PPPs) and greenhouse gas emissions. Due to the complex nature of environmental systems, the direction in which the substance flows are affected remains unclear, as does the strength of the effects. In this literature review, the focus is on the most relevant site-specific factors that affect the soil moisture regime, erosion, nitrogen (N) and phosphorus (P) fluxes, and PPP fluxes under undrained and drained conditions. The considered factors are the topography, soil characteristics, drainage types, rainfall characteristics and land management. Case studies from temperate climate zones represent the basis of the discussion, with a focus on continental Europe and the USA. In most cases, drainage enhances the total annual water flows from arable fields, while the effects on peak flows were variable, with the local topography playing a crucial role. There exists a certain level of consensus in the literature that subsurface drainage methods reduce the risk of erosion, while surface drainage may increase erosion at the edge of drainage channels. Nitrogen fluxes are generally enhanced following drainage. This is especially true for organic soils with large stores of organically bound N and, therefore, a high loss potential. For P losses, the trend goes in the opposite direction, with generally reduced losses seen following drainage installation. Similar findings are expected in relation to PPP losses. However, these trends may reverse on flat terrain, where subsurface drainage may reduce the on-site retention of these compounds. Overall, the literature reveals the patterns by which drainage affects hydrology, nutrient and PPP fluxes, although it is also evident that the combination of site-specific factors is influential. This hence needs to be considered as part of any risk assessment or management decisions.