Straw return (SR) has been widely recommended as a conservation agricultural practice in China. However, the effects of SR on crop yield and soil properties are inconsistent across studies of rice–oilseed rape cropping systems in China. This study aimed to investigate the effects of SR on crop yield and soil nutrient content in a rice–oilseed rotation system, and to understand the mechanism of straw return on the difference in yield increases between rice and oilseed rape. Additionally, suitable climate factors, soil properties, and agricultural practices were identified to achieve maximum increases in yield and soil nutrients in a rice–oilseed rotation under SR. This paper is based on a meta-analysis of 1322 observations from 83 peer-reviewed studies to evaluate the effects of climate, initial soil conditions, and agricultural management practices on rice and oilseed rape yields and soil nutrients under SR. The results showed that the responses of oilseed rape and rice yield remained positive, with 12.37% and 6.54% increases, and were significantly higher under SR than the control (no SR). Moreover, SR significantly increased the contents of several soil nutrients (soil organic carbon (SOC), total nutrients, available nutrients) and microbial biomass carbon (MBC) and nitrogen (MBN). Interestingly, the increase in crop yields was attributed to the increase in SOC, total nitrogen, and available potassium. Additionally, the increase in yields was mainly affected by climate factors, initial soil properties, and agronomic practices. For example, both mean annual temperature (MAT) and mean annual precipitation (MAP) had a positive correlation with crop yield increases under SR (p < 0.01). Initial soil conditions such as low SOC and total nitrogen content were more suitable for increased rice yield under SR, while the opposite was true for increased oilseed rape yield. Without fertilization, the SR did not significantly improve crop yield and soil nutrients, while it was more pronounced with N fertilization at 150–180 kg hm−2. The positive effect of SR on crop yields is more evident with plowing tillage, whereas the SR caused the highest increase in soil nutrients with the no-tillage condition. These findings have important implications for further improving crop yield, SOC, and soil nutrients in the Chinese rice–oilseed cropping system through straw return.