Improvement of elite safflower genotypes for drought-tolerance is hampered by a deficiency of effective selection criteria. The present study evaluated 100 genotypes of safflower in terms of their drought tolerance over a period of three years (2016–2018) under both non-stress and drought-stress conditions. The eight drought-tolerance indices of tolerance index (TOL), mean productivity (MP), geometric mean productivity (GMP), stress susceptibility index (SSI), stress tolerance index (STI), yield stability index (YSI), drought resistance index (DI), and harmonic mean (HARM) were calculated based on seed yield under drought (Ys) and non-drought (Yp) conditions. A high genetic variation was found in drought tolerance among the genotypes studied. The MP, GMP, and STI indices were able to discriminate between tolerant and drought-sensitive genotypes. Plots of the first and second principal components identified drought-tolerant genotypes averaged over the three study years. Cluster analysis divided the genotypes into three distinct groups using the drought tolerance indices. Ultimately, eight genotypes (namely, G3, G11, G13, G24, G33, G47, G58, and G61) from different origins were detected as more tolerant to drought stress suitable for use in safflower breeding programs in drought-affected areas. The most tolerant and susceptible genotypes could be exploited to produce mapping populations for drought tolerance breeding programs in safflower.