The present study was undertaken to determine the effect of different sowing strategies and spring nitrogen (N) fertilizer rates on the technological quality of winter wheat (Triticum aestivum L.) grain in terms of its milling quality, protein complex quality, and enzyme activity (falling number). Winter wheat grain for laboratory analyses was produced in a small-area field experiment conducted between 2018 and 2021 in the AES in Bałcyny (53°35′46.4″ N, 19°51′19.5″ E, NE Poland). The experimental variables were (i) sowing date (early: 6 September 2018, 5 September 2019, and 3 September 2020; delayed by 14 days: 17–20 September; and delayed by 28 days: 1–4 October), (ii) sowing density (200, 300, and 400 live grains m−2), and (iii) split application of N fertilizer in spring (40 + 100, 70 + 70, and 100 + 40 kg ha−1) at BBCH stages 22–25 and 30–31, respectively. A sowing delay of 14 and 28 days increased the bulk density (by 1 and 1.5 percent points (%p), respectively), vitreousness (by 3 and 6%p, respectively), and total protein content of grain (by 1% an 2%, respectively). A sowing delay of 14 days increased grain hardness (by 5%), the flour extraction rate (by 1.4%p), and the falling number (by 3%) while also decreasing grain uniformity (by 1.9%p). In turn, a sowing delay of 28 days increased the wet gluten content of grain (+0.5–0.6%p) and improved the quality of the protein complex in the Zeleny sedimentation test (+1.5%). An increase in sowing density from 200 to 300 live grains m−2 led to a decrease in grain uniformity (by 2.6%p), the total protein content (by 1.5%), and the wet gluten content of grain (by 0.7%p). A further increase in sowing density decreased grain vitreousness (by 1.4%p). The grain of winter wheat fertilized with 40 and 100 kg N ha−1 in BBCH stages 22–25 and 30–31, respectively, was characterized by the highest hardness (64.7), vitreousness (93%), flour extraction rate (73.9%), total protein content (134 g kg−1 DM), wet gluten content (36%), and Zeleny sedimentation index (69 mL).