In the North China Plain, drip irrigation is gradually used in winter wheat production, and the improper management of water and fertilizer aggravates the risk of crop instability and groundwater pollution. A lysimeter experiment with three levels of fertilization timing (T1 = beginning; T2 = middle; and T3 = end of the irrigation cycle) and two irrigation rates (W1 of 30 mm and W2 of 20 mm) was carried out to investigate the effects of irrigation rate and fertilization timing on the soil NO3−-N distribution, crop development, yield, and water–nitrogen usage efficiency of winter wheat. The results indicated that, under the condition of delayed fertilization timing (T2 and T3), the trend of NO3−-N migration to the edge of moist soil became more apparent. The treatments of irrigation rate and fertilization timing significantly affected the plant height, water–nitrogen utilization efficiency, aboveground biomass, grain yield, and leaf area index. The maximum grain yield of 7688.67 kg ha−1 was found at W1T2, which had a nitrogen partial factor productivity (NPFP) of 32.04 kg kg−1. Moreover, W1T2 did not result in a significant reduction in irrigation water use efficiency (IWUE) (4.27 kg m−3) in comparison with other treatments (4.00–5.43 kg m−3). Based on crop growth, N uptake, yield, IWUE, and NPFP, the irrigation rate of 30 mm combined with fertilization in the middle of the irrigation duration could be considered as suitable irrigation and nitrogen timing for drip-irrigated wheat.