The deposition and retention of pesticide sprays on the surface of hydrophobic plant leaves is a major agricultural challenge, and the deposition of hydrophobic surfaces caused by plant leaf diseases is also a major agricultural problem. Many recent studies have focused on evaluating the effect of adding surfactants to water rather than to pesticide solutions to increase the deposition and retention of spray liquids. Here, we report a strategy to solve the problem of deposition and retention by studying the impact of the behavior of pesticide droplets with added surfactants and performing kinetic analysis on cucumber leaves with powdery mildew. The reduction in the bounce and splash of the pesticide droplets was analyzed by combining the pinning site formed in the retraction stage and the viscous dissipation in the rebound stage. In the practical application of the pesticide spray, we can clearly see that the bounce, splash, and powdery mildew spore ejection decreased when surfactants were added to the pesticide spray that was used on the cucumber leaves, and the adhesion and retention increased. The proposed comprehensive method is helpful for understanding the interactions between pesticide spray droplets and the surface of cucumber leaves with powdery mildew.