Water deficiency is one of the most severe abiotic stresses in rainfed dry lands and limits crop productivity. Exogenous applications of salicylic acid (SA) have been applied to mitigate the adverse effects of water-deficit stresses, but the relative efficacy of different derivatives of SA in enhancing water-deficit tolerance along with the underlying physio-biochemical mechanism and yield of crops is not well documented. Field experiments were conducted to ascertain the relative efficacy of exogenous application of three plant bioregulators (PBRs) [SA, thiosalicylic acid and 5-sulfosalicylic acid (SSA)], each at three concentrations (0.5, 1.0 and 1.5 mM), on the growth, physio-biochemical characteristics and yield of cluster bean under rainfed conditions. Based on a 2-year field experiment, the application of PBRs enhanced yield (from 8 to 16%). The yield enhancement with the application of PBRs was associated with elevated water content (from 9 to 17%), membrane stability (from 12 to 18%) and antioxidant enzyme activity (from 12 to 33%) and reduced lipid peroxidation (from −15 to −34%) in leaves. The effects of PBRs were conditionally type and concentration dependent. The application of SSA at a rate of 1 mM was more effective in enhancing water-deficit tolerance and improving the yield of cluster bean under water shortage conditions. This study provides empirical evidence of the potential for the application of SA and its derivatives to enhance crop yields under drought conditions. The results have direct implications for sustainable crop production for similar regions of the world facing water deficits.