The European Union Water Framework Directive (2000/60/EC; WFD) aims to achieve a good ecological and chemical status of all bodies of surface water by 2027. The development of integrated guidance on surface water chemical monitoring (e.g., WFD Guidance Document No. 7/19) has been transferred into national German law (Ordinance for the Protection of Surface Waters, OGewV). For the majority of compounds, this act requires monthly sampling to assess the chemical quality status of a body of surface water. To evaluate the representativeness of the sampling strategy under the OGewV, high-frequency online monitoring data are investigated under different sampling scenarios and compared with current, monthly grab sampling data. About 23 million data points were analyzed for this study. Three chemical parameters (dissolved oxygen, nitrate-nitrogen, and chloride concentration) and discharge data were selected from four catchments of different sizes, ranging from 51,391 km² to 84 km² (Elbe, Vereinigte Mulde, Neiße and two stations at Lockwitzbach). In this paper, we propose short-term online-monitoring (STOM) as a sampling alternative. STOM considers the placement of online sensors over a limited duration and return interval. In general, we: (I) compare the results of conventional grab sampling with STOM, (II) investigate the different performance of STOM and grab sampling using discharge data as a proxy for analyzing event-mobilized pollutants, and (III) investigate the related uncertainties and costs of both sampling methods. Results show that STOM outperforms grab sampling for parameters where minimum/maximum concentrations are required by law, as the probability of catching a single extreme value is higher with STOM. Furthermore, parameters showing a pronounced diurnal pattern, such as dissolved oxygen, are also captured considerably better. The performance of STOM showed no substantial improvements for parameters with small concentration variability, such as nitrogen-nitrate or chloride. The analysis of discharge events as a proxy parameter for event-mobilized pollutants proves that the probability of capturing samples during events is significantly increased by STOM.