The impact of drought events on the growth and yield of wheat plants has been extensively reported; however, limited information is available on the changes in physiological characteristics and their effects on the growth and water productivity of wheat after repeated drought stimuli. Moreover, whether appropriate drought stimulus can improve stress resistance in plants by improving physiological traits remains to be explored. Thus, in this study, a pot experiment was conducted to investigate the effects of intermittent and persistent mild [65%–75% soil water-holding capacity (SWHC)], moderate (55%–65% SWHC), and severe drought (45%–55% SWHC) stress on the growth, physiological characteristics, yield, and water-use efficiency (WUE) of winter wheat. After the second stress stimulus, persistent severe drought stress resulted in 30.98%, 234.62%, 53.80%, and 31.00% reduction in leaf relative water content, leaf water potential, photosynthetic rate (Pn), and indole-3-acetic acid content (IAA), respectively, compared to the control plants. However, abscisic acid content, antioxidant enzyme activities, and osmoregulatory substance contents increased significantly under drought stress, especially under persistent drought stress. After the second rehydration stimulus (ASRR), the actual and maximum efficiency of PSII and leaf water status in the plants exposed to intermittent moderate drought (IS2) stress were restored to the control levels, resulting in Pn being 102.56% of the control values; instantaneous WUE of the plants exposed to persistent severe drought stress was 1.79 times that of the control plants. In addition, the activities of superoxide dismutase, peroxidase, catalase, and glutathione reductase, as well as the content of proline, under persistent mild drought stress increased by 52.98%, 33.47%, 51.95%, 52.35%, and 17.07% at ASRR, respectively, compared to the control plants, which provided continuous antioxidant protection to wheat plants. This was also demonstrated by the lower H2O2 and MDA contents after rehydration. At ASRR, the IAA content in the IS2 and persistent moderate drought treatments increased by 36.23% and 19.61%, respectively, compared to the control plants, which favored increased aboveground dry mass and plant height. Compared to the control plants, IS2 significantly increased wheat yield, WUE for grain yield, and WUE for biomass, by 10.15%, 32.94%, and 33.16%, respectively. Collectively, IS2 increased grain growth, yield, and WUE, which could be mainly attributed to improved physiological characteristics after drought-stimulated rehydration.