Crop production systems contribute significantly to maintaining global food security. These systems often involve the cultivation of single cultivars in highly homogenised environments to meet demands. Agriculturally important plant fungal pathogens can be destructive constraints in such systems. Integrated disease management strategies comprising the tactical use of cultural, chemical and host genetic controls are deployed to reduce the impact of plant pathogens. The homogenous nature of these cropping systems combined with evolutionary forces on the often-flexible fungal genome increases the potential for rapid adaptation of plant pathogens to current integrated disease management practices. This review explores the genomic features of the fungal genome (such as transposable elements and copy number variation) that influence the adaptation of pathogen populations in cropping systems. Furthermore, the interactions between such genomic features and the evolutionary forces that drive fungal adaptation are discussed relative to the three major components of integrated disease management in agricultural systems. This review specifies the need for a cohesive analysis of fungal plant pathogens within cropping systems to maintain sustainable food production in the face of future pathogen adaptation and evolution.