The fungal ear rot of maize cultivated in temperate areas is mainly due to the Fusarium species. The use of insecticides against European Corn Borer (ECB) reduces the severity of fungal ear rot as well as the fumonisin (FB) and moniliformin (MON) levels in maize kernels at harvest, which in turn results in a lowering of their effect on deoxynivalenol (DON) control. However, the direct fungicidal control of ear rot has rarely been implemented for maize, and the first studies reported conflicting results on the reduction of mycotoxins. In the present experiment, field trials were carried out in North Italy over three growing seasons to study the effect of fungicide application timings on maize to control mycotoxins, considering the interaction of the application with the insecticide treatment, according to a full factorial split plot design. The mycotoxin content was determined through LC−MS/MS analysis. The field trials showed a significant reduction in ECB severity (75%), fungal ear rot severity (68%), Fusarium Liseola section infection (46%), FBs (75%) and MON (79%) as a result of the insecticide application for all the years, while the DON content increased by 60%. On the other hand, a fungicide application alone or applied in plots protected by an insecticide was never effective for the fungal symptoms, infection or mycotoxin content. The results confirm that a correct insecticide application to control ECB damage is the most effective agrochemical solution for the control of fungal ear rot, FBs and MON.