The modern, risk-based approach requires that only those pollutants which are likely to be present in a given water supply should be monitored in drinking water. From this perspective, defining an adequate approach to the monitoring of pesticides in areas with intensive agriculture is currently one of the greatest issues of regulation. This article shows the development and detailed results of pesticide monitoring in drinking water in the Czech Republic (CR). More than 4000 water supply zones serving around a 9.5 million population are routinely monitored, with nearly 250 thousand analyses of over 200 different pesticides and their metabolites being performed every year, with a non-compliance rate of ca. 0.3%. In 2017, pesticides accounted for most derogations in the CR, concerning a total of 64 water supply systems serving more than a 250 thousand population. A representative survey targeting 21 selected chemicals showed that 75% of water supply systems contained up to 11 pesticides per sample. The most commonly found were metabolites of the herbicides used to protect oilseed rape, maize, and sugar beet: acetochlor ESA, alachlor ESA, metazachlor OA, and chloridazon-desphenyl. The health risk assessment did not reveal any risks from these chemicals, even at the highest levels detected or in the most abundant mixtures, to the most vulnerable population (infants). Nevertheless, the increased presence of pesticides undermines the public's trust in drinking water safety.