The aim of the study was to examine the variation and breeding effects on the stay-green traits, and to identify the relationship between the different growing seasons and grain yield of the Pannonian winter wheat. The experiment was carried out with a historical set of 25 winter wheat cultivars during four growing seasons, in a typical Pannonian location at the experimental field of the Institute of Field and Vegetable Crops, Novi Sad, Serbia. The results demonstrated a linear wheat grain yield progress at the rate of 45.7 kg ha −1 yr −1 , along with significant variations observed in most stay-green traits due to increased capability of modern wheat cultivars to retain prolonged crop greenness. Furthermore, significant positive correlations between the onset and mid senescence and grain yield in three out of four studied seasons showed that the prolonged senescence led to grain yield increase. Modern wheat cultivars showed an increase of crop greenness at anthesis, onset and mid senescence, and the stay-green interval, as well as a faster senescence rate. Moreover, the stay-green interval was positively correlated with grain yield in each growing season, while the senescence rate was significantly positively correlated with grain yield in the three growing seasons. Furthermore, all examined traits, except the endpoint of senescence (N10), were significantly negatively correlated with anthesis time during all growing seasons. Knowledge about the positive correlations between the prolonged stay-green traits and grain yield could be used for adjusting post-anthesis senescence traits and implemented in winter wheat breeding programs under the climate conditions of the Pannonian Plain. • Significant progress in grain yield over the year of cultivar release. • Modern cultivars have higher NDVI values and prolonged stay green duration compared to the older cultivars. • Close relationship between the stay-green duration indicators with grain yield. • Anthesis date is negatively related to the duration of senescence stages.