Drainage ponds have the potential to serve as long-term interface measures primarily for flood control, and mass retention. They are often considered as promising supplements for the mitigation of drainage pipe loads to improve the water quality in agricultural landscapes. In this study, a highly dynamic drainage pond system with non-steady inflows and groundwater interaction was modified and investigated regarding its potential for pesticide and transformation product (TP) retention. For this purpose, two 104-day monitoring campaigns were conducted before and after pond modification. Field experiments with fluorescent tracers, Uranine and Sulforhodamine-B, proved that structural modifications improved the hydraulic functionality of the ponds. The effective volume (Ɛ) increased from 20% to almost 100% in the modified pond and the mean hydraulic residence time (τ) was ten times longer. After a dry period, pesticide retention was high during slow refilling of the ponds, still TP loads posed a risk by infiltration into shallow groundwater due to the permeable ground. During wet periods, short nominal detention times together with high inflows led to rare high retention rates through peak attenuation. Moderate inflows resulted in extremely variable retention values, owing to the small pond storage capacity. Along with this, the total retention efficiency after modification reached up to 38% for mobile, 29% for sorptive pesticides, and 32% for mobile TPs. To achieve the best performances for ponds as natural landscape elements, they should be analysed for their hydrological functionality as a prerequisite and then modified for delayed pesticide and TP transport. Then, dynamic drainage ponds can utilize their full potential regarding mitigation of pesticide and TP loads in agricultural catchments.