Problems related to the environment are increasingly com- monly known and consequently also technology is adapting to find suit- able solutions. The ancestral technique of crop rotation was identified as a solution to address the problems related to pollution due to inten- sive food production (i.e. using fertilizers and pesticides). To ensure that this technique can actually improve food production, it is necessary to understand how modern technologies can support it; in particular the analysis of crop rotation can support farmers in decision making process and the optimization of farm management practices. This paper aims to exploit how predictive process monitoring techniques can contribute (with real-time monitoring) to more accurate and adaptive crop rotation strategies and contribute to leverage Agriculture 4.0. This paper serves as position paper with the aim of posing research questions to be further investigated and whom answer can contribute to the development of the research field.