The climate variability and changes in rainfall and temperature patterns caused by climate change have a negative impact on rainfed cereal production because these crops are not only exposed to, but depend on, extreme climate conditions. So it is imperative to implement techniques and methodologies that enable farmers to adapt their crops to the new circumstances. Two simple and cost-effective methods for adjusting a cropping system to this situation could involve altering crop sowing dates and/or selecting varieties with different growth cycles that are less susceptible to the extreme weather events that occur in critical phenological stages of their development. In our experiment, we examined the behavior of six different wheat (Triticum aestivum L.) genotypes (with varying growth cycles) sown at three times (October, November, February) during a 4-year field trial. The results suggest that better selection of sowing date and genotype could be able to improve yield and grain quality. However, further studies should be performed about the current year forecast, and must consider specific impacts of water availability and temperatures in specific phenological phases, to achieve better crop management selection at the beginning of each season both these conditions and very different soil/weather conditions.