Winter cereals provide distinct advantages over spring cereals. This includes higher grain yields and limiting weed pressure, soil erosion, and exposure to diseases and insect pests, which are regularly serious threats to spring cereals. The agronomic system for winter cereals in western Canada is built around ensuring that the crop survives winter. Critical to this system is uniform plant stands reaching an optimum growth stage to maximize cold tolerance and no-till production systems that maintain insulating snow cover through the use of stubble from a previous crop. Breeding has led to significant increases in grain yield for both winter wheat and fall rye, however, no progress in cold tolerance improvement has been realized by winter cereal plant breeders over the same period. Progress in fall rye breeding has led to more recent varieties having reduced lodging and plant height and increased seed size and test weight. For winter wheat, the incorporation of robust disease resistance packages ensures adaptation across the prairies and also enables the potential to lengthen the growing season and increase yield. Looking forward, winter cereals provide the potential to take advantage of predicted western Canadian climate change scenarios and play a significant role in productivity increases through utilizing double or relay cropping practices, which are currently being developed. Continued improvement in winter cereal agronomic practices and the introduction of new varieties means that winter cereals will continue to play an important role in maximizing productivity and extending the growing season in western Canada.