Sustainable and profitable crop production has become a challenge due to frequent weather extremes, where unstable crop yields are often followed by the negative impacts of agronomic practices on the environment, i.e., nitrate leaching in irrigated and nitrogen (N)-fertilized crop production. To study this issue, a three-year field study was conducted during quite different growing seasons in terms of weather conditions, i.e., extremely wet, extremely dry, and average years. Over three consecutive years, the irrigation and N fertilizers rates were tested for their effect on grain yield and composition, i.e., protein, starch, and oil content of the maize hybrids; soil N level (%); and nitrate leaching. The results showed that the impact of the tested factors and their significance was year- or weather-condition-dependent. The grain yield result stood out during the extremely wet year, where the irrigation rate reduced the grain yield by 7.6% due to the stress caused by the excessive amount of water. In the remainder of the study, the irrigation rate expectedly increased the grain yield by 13.9% (a2) and 20.8% (a3) in the extremely dry year and 22.7% (a2) and 39.5% (a3) during the average year. Regardless of the weather conditions, the N fertilizer rate increased the grain yield and protein content. The soil N level showed a typical pattern, where the maximum levels were at the beginning of the study period and were higher as the N fertilizer rate was increased. Significant variations in the soil N level were found between weather conditions (r = −0.719) and N fertilizer rate (r = 0.401). Nitrate leaching losses were expectedly found for irrigation and N fertilizer treatments with the highest rates (a3b3 = 79.8 mg NO3− L).