An exact experiment, established in a system of randomized blocks, was aimed at determining the effect of crop rotation and 29-year cereal monoculture on the yield and quality of winter wheat grain as well as on straw yield, crop infestation with weeds, contents of organic C and total N in the soil, and the number of earthworms in the soil. Winter wheat was sown in two systems of crop succession: (1) in crop rotation (CR), and (2) in a cereal monoculture (CM). Winter wheat cultivation in the CM system resulted in a decrease of grain yield by 32%, compared to the CR system. Its grain yield reduction in the CM system was due to a lower number of spikes m −2 , lower 1000 grain weight, shorter spikes, and lower grain weight per spike, than in the CR system. Wheat grain from the CM system was characterized by a lower content of wet gluten, lesser grain uniformity and grain volume weight, and contained more total ash than the grain from the CR system. The number and air-dry weight of weeds were higher in the CM than in the CR system by 57.1% and 75%, respectively. Differences were also demonstrated in the species composition of weeds. The soil samples collected from the CM plot contained less organic C and total N than the samples derived from the CR system. Soil samples from the CM system had also a lower number of earthworms compared to the CR soil samples.