Fresh fruit bruising caused by mechanical impact is the most problematic effect of mechanical postharvest processing of tomatoes. The conventional postharvest process of tomato fruit (Solanum lycopersicum L.) handling was surveyed from harvest to shipping preparation at a farm in Toechon in the Republic of Korea. Acceleration sensors located on the harvest boxes and fruit skin showed that the most severe impact forces (>10 g) occurred while fruit was moved in and out of the harvest box. Next, multivariate analysis was used to evaluate nondestructively the susceptibility of tomatoes to bruising by developing five estimation models incorporating quality factors and the presence of bruising resulting from peak contact forces. Linear regression models, artificial neural network (ANN) regression models, and a logistic regression model were built; the primary dependent variables were the rates of weight loss and firmness loss, and impact-induced bruising. The impact force was controlled by using a pendulum, which produced four levels of impact force on tomato fruit. Increasing the relative humidity (RH) and firmness, and decreasing the temperature and degree of weight loss decreased tomato fruit bruise damage. In addition, the proposed drop–impact measurement technique, with multivariate analysis, can be used to evaluate tomato quality nondestructively.