This study examined the effects of late sowing, water restrictions, and interannual weather variations on wheat grain yield and quality through field trials in Spain over two growing seasons. Delayed sowing and water scarcity significantly reduced yields, with grain quality mainly affected under rainfed conditions. Early-maturing varieties performed better in these conditions, benefiting from lower temperatures and extended grain-filling periods, leading to higher solar radiation interception, potentially increased photosynthetic activity, and improved yields. These varieties also saved water through reduced total cumulative evapotranspiration from sowing to maturity (ETo TOT), which was advantageous in water-limited environments. In contrast, late-maturing varieties were exposed to higher maximum temperatures during grain filling and experienced greater ETo TOT, leading to lower yields, reduced hectoliter weight, and a lower P/L ratio (tenacity/extensibility). This study highlighted the importance of optimizing temperature exposure and evapotranspiration for improved grain yield and quality, especially under climate change conditions with higher temperatures and water shortages. Notably, it established, for the first time, the importance of phenology on wheat quality of different varieties, suggesting that targeted selection for specific phenology could mitigate the negative impacts of heat stress not only on grain yield but also on grain quality.