Investigating the effects of natural rainfall on the soil moisture for sloping farmland is extremely important for comprehending a variety of hydrological processes. Rainfall regimes can elicit different responses to soil moisture at the depth of soil layers, and the responses may differ depending on the landscape position of the sloping farmland. This paper utilized the surface runoff natural rainfall and soil moisture measured on sloping farmland with conventional tillage and contour tillage in the red soil area of China to investigate the influence of natural rainfall events on soil moisture content and to evaluate if the response results were consistent across the four rainfall regimes. Natural rainfall events were classified into different four regimes in line with rainfall duration, rainfall amount, and the maximum 30 min rainfall intensity (I30) by the k-means clustering method, including advanced, intermediate, uniform and delayed regimes. The result showed that the advanced regime was the predominant one in the study area, which represented 45.9% of the total rainfall events. The rainfall regimes influenced the surface runoff coefficient and runoff depth on sloping farmland for conventional and contour tillage, with the uniform regime generating the highest runoff coefficient (5.20% and 5.82%) and runoff depth (2.00% and 2.05%), respectively. For the conventional tillage, soil moisture at a depth of 0–20 cm increased appreciably when the rainfall amount was larger than 20 mm and larger than 30 mm for the advanced regime. For the contour tillage, soil moisture in 20–40 cm layer increased for the advanced regime when the rainfall amount was larger than 15 mm and 30 mm, while the values were modified with rainfall duration and the antecedent dry day (ADD). A longer rainfall duration had a more obvious effect on soil moisture increasing in deep soil. At a depth of 20 cm, the ADD showed an appreciably positive correlation with the increment in soil moisture, which means that a brief ADD produces a compounding effect for a natural rainfall event. The present results underline the complexity of the effect of the rainfall events on soil moisture under two tillage measures for different rainfall regimes and suggest that the advanced regime significantly affects the distinction of soil moisture and the contour tillage can effectively reduce soil water loss and enhance water storage on the sloping farmland with red soil, presenting a theoretical basis for local soil and water conservation research and sloping farmland conservation tillage management.