Evidence from an array of dryland systems suggests that chickpea (Cicer arietinum L.) grain yield could be improved through better phenological adaptation. However, information on the relationship between phenology and Ascochyta response genes, and their possible interaction with biomass and grain yield, is missing. Accordingly, the aim of the present study was to determine the associations between the above factors and biomass and grain yield in chickpea. To that end, standard Israeli cultivars and advanced generation bulked progeny from the cv. Hadas × ICC5810 cross were used. Hadas is a late-flowering, high-yielding Israeli kabuli (0.45 g/seed) cultivar with moderate field resistance to Ascochyta blight, whereas ICC5810 is a day-neutral desi (0.15 g/seed) genotype with a strong temperature response, from India. Higher yields were observed among the late-flowering bulks of the Hadas × ICC5810 progeny. No relationship between the Ascochyta response and biomass and grain yield was observed. No interaction between the phenology and Ascochyta response grouping on biomass and grain yield was observed. The results demonstrate the feasibility of combining Ascochyta resistance with earlier flowering and its potential to improve chickpea adaptation to dryland systems.