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Continuous tillage cultivation positioning trials can provide the basis for maintaining soil health, improving resource utilization efficiency and crop productivity, and achieving sustainable agricultural development. In this study, changes in soil stability and water–holding capacity characteristics were measured under different tillage cultivations from a multi–year microscopic perspective and analyzed to evaluate selected key indicators. Continuous monitoring of rainfall utilization efficiency and yield was carried out for five years. Here, we discuss the role of conservation tillage in buffering and stabilizing rainfall precipitation pattern on the fluctuation and uncertainty of soil water retention and water supply capacity and soil quality. The study was carried out on dryland areas of the Loess Plateau in northern China with eight tillage systems established in 2016: no–tillage (NT); no–tillage and straw (NTS); subsoiling (SU); subsoiling and straw (SUS); rotary tillage (RT); rotary tillage and straw (RTS); conventional tillage (CT); and conventional tillage and straw (CTS). All treatments were applied in conjunction with continuous cropping for five years. The evaluated soil parameters were mean weight diameter (MWD), geometric mean diameter (GMD), >0.25 mm aggregate content (R0.25) of water–stable aggregates (WSAs), soil moisture characteristic curve (SMCC), specific soil water capacity (Cθ), soil organic matter (SOM), rainfall utilization efficiency (RUE), and maize yields for five consecutive years. The MWD, GMD, and R0.25 of SUS were 27.38%, 17.57%, and 7.68% more than CTS (control), respectively. Overall, SOM, average annual RUE, and average annual yields increased by 14.64%, 11.89%, and 9.59%, respectively, compared with 2016. Our results strongly suggest that conservation tillage can considerably improve these characterization indicators. SUS was more effective than CTS in the 0–40 cm soil layer at hedging against drought in the area, stabilizing crop production, and achieving sustainable agricultural development.