This study analyzes the temporal patterns of rainfed cereal phenology extracted from the GIMMS NDVI3g dataset in the main cereal-growing regions under a Mediterranean climate in Spain, Portugal, France and Italy during the period 1982–2022. The series before and after the beginning of the 21st century were analyzed separately. Phenological parameters were extracted using the modified dynamic threshold method, and their trends were analyzed. Correlation analyses were performed to study the relationships among these parameters and to analyze the influence of hydroclimatic variables on the start (SOS) and end (EOS) of the growing season. Results showed a temporal reversal in phenological trends between both study periods, coinciding with the global warming hiatus. In the first period (1982–2002), SOS and EOS advanced (−7.5 and −3.1 days, respectively), and the length of growing season (LOS) increased. However, during the second stage (2003–2022), SOS and EOS were delayed (7.5 and 1.7 days, respectively), and LOS decreased. Similar dynamics were observed for the influence of the hydroclimatic variables on SOS and EOS, stronger in the first period and weaker in the second. This study provides valuable information on the phenological dynamics of rainfed cereals that may be useful for their management and planning in climate change scenarios.