Grain filling is the key stage for achieving high grain yield. Subsoiling tillage has been widely used as a conservation tillage method in the maize planting region of China. This study was conducted to explore the effects of subsoiling on the grain filling characteristics of maize varieties of different eras. Five typical maize varieties from different eras (1970s, 1980s, 1990s, 2000s and 2010s) were used as trial materials with two tillage modalities: rotation tillage and subsoiling tillage. The characteristic parameters and rate parameters of grain filling were compared and analyzed using the selected tillage modalities. The results showed that the grain filling parameters of the 2010s variety were better than those of the other varieties, and these differences mainly manifested in the filling rate parameters of the rapidly increasing and slowly increasing periods. In comparison with rotation tillage, subsoiling improved the maximum grain filling rate and the grain growth during the period of the maximum grain filling rate to different degrees. In addition, subsoiling delayed the appearance time of the maximum grain filling rate, extended the grain filling duration, and improved the mean filling rate. These differences are major reasons for the significant increase in 100-kernel dry weight at harvest for subsoiling in comparison with rotation tillage. Moreover, subsoiling enhanced the filling rate parameters during the rapidly increasing and slowly increasing periods. The filling stage filling duration and filling rate of maize varieties of different eras showed different responses to subsoiling. For example, the grain filling rate parameters of the 2010s variety during the rapidly increasing period were more sensitive to subsoiling in comparison with those of the other varieties.