The winter fallow period common in annual cropping systems leaves soils vulnerable to erosion and nutrient loss, especially to nitrogen (N) leaching. This vulnerability can be mitigated with perennial crops that have living roots in the ground year-round. The mechanisms, magnitude, and consistency with which perennial crops retain N are not clear. We used an experiment to test whether a perennial crop, miscanthus (Miscanthus × giganteus Greef et Deu.), would leach less N than continuous maize (Zea mays L.) and how soil net N mineralization (Nmin) may explain observed leaching under varied environment and management conditions. The experiment included three crossed factors: 1) cropping system (maize, juvenile miscanthus = 1-2 y old, mature miscanthus = 3-4 y old); 2) N fertilization (0 and 224 kg N ha-1); and 3) environment (four site-years at two locations in Iowa, USA that differed in climate and soil fertility). We measured N cycling dynamics, including: inorganic soil N (ammonium + nitrate), in situ Nmin, N leaching, crop N uptake, and calculated system N use efficiency. There were many complex interactions among factors. On average, cumulative Nmin under juvenile miscanthus was 111% greater than maize, but as miscanthus matured, there was no difference in Nmin between the perennial crop and maize. There was no difference in N leaching between juvenile miscanthus and maize, but mature miscanthus decreased N leaching by 42% and 88% compared to maize (with and without N fertilization, respectively). Across all treatments, there was no relationship between Nmin and N leaching, suggesting other mechanisms are regulating N leaching. Overall, mature miscanthus shows promise as a tool to reduce N losses in areas dominated by annual row-crops.