Clarifying the response of plant phenology to drought duration is helpful for accurately interpreting and predicting carbon sinks in ecosystems. Based on the response of different phenological periods of the dominant species Stipa krylovii to monthly, seasonal, and semiannual time scale drought in the typical steppe of Inner Mongolia from 1983 to 2018, the results revealed that (1) the start of the growing season (SOS) was characterized by an advance–delay–advance pattern, and the heading stage (HOS), flowering stage (FOS), and end of the growing season (EOS) all showed consistent advanced trends, which provided additional insight into the conclusions of previous studies that found the SOS was advanced in arid and semiarid regions. (2) The response mechanism of the SOS to the timing of drought was not consistent. Among the response mechanism, the SOS was delayed because of the January–February drought at different time scales but advanced because of the April drought at different time scales. The HOS/FOS was delayed by the June–July drought at different time scales, and the EOS was advanced by the August–September drought at different time scales. (3) More importantly, the SOS, HOS, FOS, and EOS were affected by predrought and its persistence, and the effects were greater the closer to the phenological periods that drought occurred. (4) At the monthly scale, droughts in January, June, and August were the critical drought periods affecting the SOS, HOS/FOS, and EOS, while seasonal and semiannual scale droughts in February, June–July, and September were the critical periods affecting the SOS, HOS/FOS, and EOS. The results of this study enrich our understanding of how drought at different time scales affects different phenological periods, providing a basis for improving plant phenological models.