Shading stress caused by plum rain season, which overlapped with grain filling process of fresh waxy maize in Southern China, significantly affected crop productivity. In order to investigate the effects of shading at different stages after pollination on the yield, accumulation, and remobilization of dry matter and nitrogen (N) in fresh waxy maize, field experiments were conducted, including shading at 1–7 (Z1), 8–14 (Z2), 15–21 (Z3), and 1–21 (Z4) days after pollination in 2020 and 2021. The results showed that shading reduced the fresh ear and grain yield and increased moisture content in Suyunuo5 (SYN5) and Jingkenuo2000 (JKN2000) compared to natural lighting treatment (CK). The ear yield decrease was more severe in Z4 (43.5%), followed by Z1 (29.7%). Post-silking dry matter and N accumulation and remobilization were decreased under shading stress, and those were lowest in Z4, followed by Z1. The remobilization of pre-silking dry matter and N were increased by shading stress, and the increase was highest in Z4, followed by Z1. The harvest index of dry matter and N was lowest in Z4 and second-lowest in Z1. In conclusion, shading decreased yield by affecting accumulation and remobilization of post-silking dry matter and N, and the impact was more serious when it introduced early during grain filling stage in fresh waxy maize production.