Dissolved reactive phosphorus (DRP) loss from agricultural soils can negatively affect water quality. Shallow subsurface pathways can dominate P losses in grassland soils, especially in wetter months when waterlogging is common. This study investigated the processes controlling intra- and inter-event and seasonal DRP losses from poorly drained permanent grassland hillslope plots. Temporal flow related water samples were taken from surface runoff and subsurface (in-field pipe) discharge, analysed, and related to the likelihood of anaerobic conditions and redoximorphic species including nitrate (NO3−) over time. Subsurface drainage accounted for 89% of total losses. Simple linear regression and correlation matrices showed positive relationships between DRP and iron and soil moisture deficit; and negative relationships between these three factors and NO3− concentrations in drainage. These data indicate that waterlogging and low NO3− concentrations control the release of P in drainage, potentially via reductive dissolution. The relationship between DRP and metal release was less obvious in surface runoff, as nutrients gathered from P-rich topsoil camoflaged redox reactions. The data suggest a threshold in NO3− concentrations that could exacerbate P losses, even in low P soils. Knowledge of how nutrients interact with soil drainage throughout the year can be used to better time soil N and P inputs via, for example, fertiliser or grazing to avoid to excessive P loss that could harm water quality.