Dry direct-seeded rice (DDSR) is an adaptive practice used in rainfed lowlands of tropical Asia where insufficient rainfall at the onset of the wet season makes it difficult to successfully transplant rice seedlings. However, basic guidelines for nutrient management to support DDSR are lacking. Here, we evaluated crop growth and yield in DDSR with different N fertilizers (ammonium sulfate, urea, and coated compound fertilizer) applied at different timings. The total N rate was fixed at 100 kg ha−1. On-station trials were conducted at the International Rice Research Institute, in the Philippines, during the wet seasons of 2017 and 2018, and 17 on-farm trials were conducted in nine provinces in 2018 and 2019. In the on-station trials, ammonium sulfate did not increase yield compared with urea and coated compound fertilizer in either year. Application of N fertilizers at sowing promoted plant N uptake and early shoot growth, but the effect of the timing of N application on yield was not significant. The on-farm trials showed that a uniform N management recommendation is unlikely to be effective in DDSR. Yield increased significantly with coated compound fertilizer relative to the uncoated fertilizers in clay and silty clay soils, but not in other soil types. In general, flexible timing of the first application of N, ranging from 0 to 30 days after sowing, had no significant effect on yield, but the omission of N application at sowing reduced yield by 13–25% in two trials on sandy soils with a low nutrient-holding capacity.