Prolonged waterlogging in agricultural fields has severe consequences for the crop development and growth, and could potentially lead to higher N losses. In this study, a 3.93 ha agricultural field in Denmark was separated into two parts of well-drained (WD) and poorly-drained (PD) based on the installation depth of the tile drains. The field was continuously monitored for drainage, soil water dynamics, nitrogen leaching through the drains, and grain dry matter and nitrogen yields in a 4-year period (2017–2020). Furthermore, denitrification potential of the top 1 m of the soil at both parts of the field was measured through the denitrifying enzyme activity assay, and a 1D Daisy model was utilized to capture the differences between water and nitrogen balances at WD and PD. Results indicated that on average over the 4 years, annual harvested nitrogen in the crops at PD was 14% lower compared to WD, with a significant reduction of 33% in 2017–2018, that coincided with the longest period of waterlogging at PD. Moreover, greater losses of nitrogen through leaching from drainage and other pathways were measured at the PD (109 kg N ha⁻¹ ya⁻¹) compared to the WD (95 kg N ha⁻¹ ya⁻¹). Based on the simulations, losses through preferential flow pathways to the drains dominated at PD and most of the denitrification is expected to occur within the topsoil. Future studies could significantly benefit from monitoring the redox dynamics in the top 30 cm of the PD soils, and increasing the depth of tiles drains by redrainage could reduce the N losses of poorly drained agricultural soils.