The aim of the study was to compare grain yield, grain quality, and morphophysiological parameters of three winter wheat cultivars: Kilimanjaro, Hymalaya, and Ostroga. The cultivars were grown in crop rotation after grain maize harvest, using three tillage systems: conventional (C), reduced (R), and no-tillage (N). A three-year field experiment was conducted in southeastern Poland. Compared to no-tillage, the use of conventional and reduced systems resulted in higher grain yield, increased leaf area index and relative chlorophyll content, and higher gas exchange parameters. In the conventional system, the highest grain yield was achieved by cvs. Hymalaya and Ostroga, while in no-tillage and reduced, it was cv. Hymalaya. Compared to no-tillage, the conventional system resulted in higher values of grain quality parameters, while simultaneously reducing ash content, and the reduced system promoted a better gluten index. Interactions between cultivar and tillage system demonstrated good grain quality in terms of protein, falling number, and gluten index. Gluten content above 25.0% was found in grains of cvs. Kilimanjaro and Hymalaya in the reduced and conventional systems, and cv. Ostroga in the conventional system. The dry and semi-drought periods in the 2018/2019 season were conducive to more favorable grain quality parameter values: protein, gluten, falling number, and ash. However, the resulting grain was characterized by a lower gluten index and lower physical parameters. Cvs. Hymalaya and Ostroga are recommended for cultivation in conventional and reduced tillage systems, and cv. additionally for no-tillage systems. Growing the cv. Kilimanjaro in no-tillage and reduced tillage systems, and the cv. Ostroga in a no-tillage system, will result in lower grain yields.