Deficit irrigation is a valid alternative to conventional irrigation to save water while maintaining high productivity in tomatoes. However, crop sensitivity to water stress due to deficit irrigation may change with the growth stage. To assess the physiological and agronomic responses of processing tomatoes to deficit irrigation applied at critical stages, a field experiment was conducted in a coastal site of Southern Italy, where seven irrigation treatments differing for daily evapotranspiration (ETc) restored (100%—full or 50%—deficit) and the time of watering (long-season or limited to the vegetative period or to flowering) were applied to processing tomatoes cv. Hypeel F1. Plants continuously irrigated and those irrigated only at flowering maintained higher rates of leaf transpiration (E) and stomatal conductance (gs) over those irrigated only during the vegetative period. Fruit yield was the greatest under long-season full irrigation (51 t ha−1). Severe soil water deficit during flowering, more than during the vegetative period, adversely affected crop productivity. Irrigation water use efficiency (IWUE) was maximized under long-season deficit irrigation (>19 kg m−3) or deficit irrigation during flowering (>16 kg m−3). E and gs measured at early or mid-flowering may be adopted as valuable indicators to predict crop productivity; however, they may be altered under high vapor pressure deficit (VPD). Predawn water potential, being little affected by VPD, is a more reliable parameter than leaf transpiration and stomatal conductance under these climatic conditions.