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Water stress is a major obstacle to agricultural production, significantly impacting both yield and quality. During the 2017–18 crop year in Shahriar region near Tehran, Iran, known for its dry and cold climate, a study was conducted to examine the influence of different irrigation levels on the quantitative and qualitative characteristics of various wheat cultivars. The experiment involved three irrigation levels: normal irrigation (control), withholding irrigation at the flowering stage, and withholding irrigation at the seed-filling stage as primary factors, with 21 different cultivars as secondary factors. The analysis showed that irrigation, cultivar type, and their interactions had a significant effect on grain yield, proline, total chlorophyll, carbohydrate content in the first and second internodes during flowering and ripening, as well as on SOD, CAT, GPX, MDA, DT, and D-OH-dG levels at a one percent significance level. Withholding irrigation at the flowering stage had a more severe impact compared to the seed-filling stage. The Rakhshan and Sivand cultivars yielded the highest and lowest grain yields under normal irrigation conditions, while the drought-tolerant Ofogh cultivar showed lower yields when irrigation was withheld at the flowering stage. Water stress led to increased proline levels and higher levels of SOD, CAT, MDA, DT, and D-OH-dG in wheat cultivars. The Rakhshan and Sivand cultivars were identified as drought-tolerant in this region.