The objective of the study was to determine the dynamics of the agrophysical parameters of the arable layer of dark chestnut soil under long-term continuous maize cultivation with the use of chemical soil ameliorants, as well as to evaluate the grain yield dynamics of maize hybrids of various FAO maturity groups and the efficiency of plant protection systems under surface drip irrigation in the Steppe zone of Ukraine. It was established that long-term continuous maize cultivation under surface drip irrigation in the Southern Steppe of Ukraine during 2021–2025 is possible without a significant decline in grain yield, provided that integrated pest management and chemical ameliorant application are implemented. Among the yield-stabilizing factors, plant protection systems demonstrated the greatest effect. Soil fertility maintenance measures were of secondary importance for yield stability but of primary importance for long-term soil fertility preservation. The genotype of maize hybrids, particularly their FAO maturity group and resistance to harmful organisms, played a crucial role in yield stabilization under continuous cultivation. The average grain yield of maize hybrids decreased by 1.50 t/ha (11.92%) over five years of monocropping. The smallest yield reduction was observed in hybrids with a shorter growing period when chemical ameliorants and integrated protection systems were applied. In the fifth year of continuous cultivation, grain yield of the hybrids Stepovyi (FAO 190) and Askaniia (FAO 320) decreased by 0.45 and 0.24 t/ha, respectively, whereas the hybrid Skadovskyi (FAO 290) maintained the initial yield level (13.15 t/ha). A significant yield reduction was recorded in the late-maturing hybrid Vira (FAO 430): its grain yield during the first two years was 15.43 and 15.18 t/ha, while during the subsequent three years it decreased by 0.76, 1.54, and 1.53 t/ha, respectively. The yield decline of late-maturing hybrids was associated with longer vegetation periods, prolonged pest pressure, and increased numbers of pest generations