Redesigning cropping and farming systems to enhance their sustainability is mainly addressed in scientific studies using experimental and modeling approaches. Large data sets collected from real farms allow for the development of innovative methods to produce generic knowledge. Data mining methods allow for the diversity of systems to be considered holistically and can take into account the diversity of production contexts to produce site-specific results. Based on the very few known studies using such methods to analyze the crop management strategies affecting pesticide use and their effect on farm performance, we advocate further investment in the development of large data sets that can support future research programs on farming system