Pesticides associated with the turfgrass industry have been detected in storm runoff and surface waters of urban watersheds, invoking concern of their potential environmental effects and a desire to reduce their transport to nontarget locations. Quantities of chlorpyrifos, dicamba, dimethylamine salt of 2,4-dichlorophenoxyacetic acid (2,4-D), flutolanil, and mecoprop-p (MCPP) transported in runoff from bentgrass (Agrostis palustris) fairway turf managed with solid tine (ST) or hollow tine (HT) core cultivation were compared to determine which cultivation practice is more efficient at mitigating environmental risk. Plots receiving HT core cultivation showed a 10 and 55% reduction in runoff volume and a 15 to 57% reduction in pesticide transport with runoff at 63 d and 2 d following core cultivation. Estimated environmental concentrations of the pesticides in a surface water receiving runoff from turf managed with ST core cultivation exceeded the median lethal concentration (LC50) or median effective concentration (EC50) of nine aquatic organisms evaluated. Replacing ST core cultivation with HT core cultivation reduced surface water concentrations of the pesticides to levels below the LC50 and EC50 for most these aquatic organisms, lessening risk associated with pesticides in runoff from the fairway turf. Results of the present research provide quantitative information that will allow for informed decisions on cultural practices that can maximize pesticide retention at the site of application, improving pest control in turf while minimizing environmental contamination and adverse effects associated with the off-site transport of pesticides.