Nitrate leaching from agriculture can be reduced by the choice of fertilizer and a proper timing of its application. For permanent grassland grown under temperate conditions, nitrate leaching was hypothesized to be lower from dairy cattle slurry (CS) compared to synthetic fertilizer calcium ammonium nitrate (CAN), based on differences in chemical composition, consequential effects on nitrogen (N) conversion processes in soil, and resulting differences in synchronization of (nitrate) N availability and plant N uptake. We tested the hypothesis in a two-year field experiment on cut grassland on a leaching-sensitive sandy soil, fertilized each year with 320 kg ha−1 of plant-available N from either 100% top-dressed CAN or a combination of 40% from CAN and 60% from sod-injected CS, and measured effects on grass herbage yield, herbage N uptake, and nitrate concentration in pore water at 1.0 m depth. Our results show a comparable level of herbage N uptake for both treatments, allowing for a proper comparison of nitrate leaching at a similar level of plant-available N. Average nitrate concentration in pore water in the main leaching period (over winter) was after the first (dry) growing season 44% lower for CS + CAN (41 mg l−1) compared to CAN only (73 mg l−1), and after the second (wet) growing season 35% lower for CS + CAN (32 mg l−1) compared to CAN only (49 mg l−1). Nitrogen application increased nitrate concentration at 1.0 m depth not only in winter but also in the growing season. We conclude that for permanent grasslands in temperate regions, nitrate leaching from timely applied CS may be considerably lower than from CAN, which is different from previous assumptions.