Continuous rain is the main meteorological constraint for winter wheat production in Jiangsu Province, accompanied by stresses of both waterlogging and shading. To evaluate the independent and combined effects on winter wheat at jointing stage, pot experiments were conducted using two cultivars, Ningmai 13 and Yangmai 13. Four treatments, CK (non-stressed), WA (waterlogging alone), SA (shading alone) and WS (both waterlogging and shading) were established with different durations. In the non-stressed environment, Yangmai 13 had higher production than Ningmai 13. However, Ningmai 13 had better production under stresses, indicating a better tolerance to waterlogging and shading. Comparing dry matter distribution and grain production showed that the negative effects of the stresses were in the order WA > WS > SA, demonstrating that shading had compensative effects on waterlogging at jointing stage. Results indicate that production loss of winter wheat due to continuous rain at jointing stage might be overestimated.