Two of the main causes of losses in tomato production are the greenhouse whitefly, Trialeurodes vaporariorum (Hemiptera: Aleyrodidae), and drought, which is becoming a central problem in agriculture due to global climate change. The separate effects of whitefly infestation and drought have been amply studied in many crop systems. However, less is known about their combined effects. To evaluate whether drought stress (DS) affects plant defense against whiteflies, we assessed the joint effects of whitefly infestation and DS on plant vegetative and reproductive performance in four tomato cultivars, and assessed the effects of DS on plant resistance and tolerance (compensatory ability) to whiteflies in a greenhouse experiment. Generally, we found negative effects of DS and whiteflies on plant performance, but the combined effects of DS and herbivory were not worse than those of either stress alone. In fact, plant performance under the combined effect of both stresses was usually similar to that in the presence of whiteflies without DS. Plants growing under DS had greater trichome density. However, plant resistance—as measured by whitefly population growth—decreased under DS in two cultivars and was unaffected in the other two. Compensatory ability decreased under DS in all but one cultivar. These cultivar-specific responses suggest genetic variation in resistance and tolerance to whiteflies and could be associated with differences in drought tolerance among cultivars. Our findings underscore the difficulty in predicting the combined effects of DS and herbivory and point to the need for a better understanding of the mechanisms underlying plant responses to both stresses at the molecular, cellular, and organismal levels.