Cover crops protecting soil erosion during the summer fallow in the monsoon weather may enhance dryland winter wheat yield and N relations. We examined the effects of four summer cover crops (soybean (Glycine max L., SB), sudangrass (Sorghum sudanense {Piper} Stapf, SG), soybean and sudangrass mixture (SS), and no cover crop (CK)) and three N fertilization rates (0, 60, and 120 kg N ha−1) on winter wheat yield, quality, and N relations from 2017–2018 to 2020–2021 in the Loess Plateau of China. Cover crop biomass and N accumulation, soil mineral N, and winter wheat yield, protein concentration, and N uptake were greater for SB and SS than other cover crops at most N fertilization rates and years. The N fertilization rate had variable effects on these parameters. Winter wheat aboveground biomass and grain N productivities were greater for CK than other cover crops at all N fertilization rates and years. Nitrogen balance was greater for SS than other cover crops at 60 and 120 kg N ha−1 in all years. The SS with 120 kg N ha−1 can enhance soil mineral N, winter wheat yield and quality, and N balance compared to CK and SG with or without N fertilization rates.