Pesticides used to protect agricultural crops may contaminate groundwater. This work aimed to identify the pesticides used in Lombardy, Italy, in 2016, their concentration in the groundwater and the risk for health associated with the intake of drinkable water in the adult population. The risk was evaluated for the presence of single and multiple active substances in the groundwater, calculating the hazard quotient (HQ) and the hazard index (HI), respectively. Lombardy utilises an agricultural area of 980,112 h, which is mainly cultivated with cereals (74%). Approximately 2354 pesticides (about 1.3 × 107 kg), containing 410 active substances (about 4.5 × 106 kg) were sold. There were groundwater contamination measurements in 158 monitoring points, which were investigated twice a year for 31 active substances, and a total of 9152 determinations. Only 17 currently used active substance were measured in the groundwater, among which three belonged to the 10 best-sold pesticides. The exceedance of the environmental quality standard was observed for about 1.5% determinations. The intake of contaminated water in the adult population resulted in a HQ typically ranging between 10−3 and 10−4 and a HI of about 10−3. Although the number of pesticides sold in 2016 in Lombardy was big, only a small fraction of active substances was monitored in the groundwater. Considering these monitored substances, the intake of contaminated groundwater in the adult general population posed an irrelevant risk for health.