Hole sowing is a new and efficient cultivation method with few studies. This study investigated the effects of different sowing densities and nitrogen topdressing at the jointing stage on dry matter, quality, and yield under wheat hole sowing to provide a theoretical basis for integrating wheat fertilizer and density-supporting technology. In this study, a two-factor split-plot design was used. The sowing density was the main plot, and four levels were set: D1, D2, D3, and D4 (238, 327, 386, and 386 suitable seeds·m−2). The four sowing levels were sown according to 8 grains/hole, 11 grains/hole, 13 grains/hole, and 16 grains/hole, respectively, with a row spacing of 25 cm and a hole spacing of 13.5 cm; the amount of nitrogen fertilizer applied at the jointing stage was the sub-area, with four levels: N1, N2, N3, and N4 (0, 60, 120, and 180 kg·ha−1). After two years of experimental research, the following main conclusions are drawn: the use of high sowing density and nitrogen topdressing is helpful to improve the dry matter quality of wheat spikes at the maturing stage; the sowing density had significant or highly significant effects on protein content, starch content, and sedimentation value. The yield from 2018–2019 reached a maximum of 8448.67 kg·ha−1 under D4N4 treatment, and the yield from 2019–2020 reached a maximum of 10,136.40 kg·ha−1 under D4N3 treatment. Therefore, the combination of 225 kg·ha−1 sowing density and 120–180 kg·ha−1 nitrogen topdressing at the jointing stage can be used in field production, which can help improve wheat production potential. Similarly, understanding the interaction between wheat hole sowing and different sowing densities and nitrogen topdressing amounts provides a practical reference for high-yield wheat cultivation techniques.