Postharvest losses amongst small-scale farmers in developing countries are high due to inadequate resources and infrastructure. Among the various affected crops, tomatoes are particularly vulnerable; however, studies on postharvest losses of most fruits and vegetables are limited. Therefore, this study aimed to assess postharvest tomato losses under different production systems within the small-scale supply chain using the indirect assessment (questionnaires and interviews) and direct quantification of losses. Farmers reported tomato losses due to insects (82.35%), cracks, bruises, and deformities (70.58%), and diseases (64.71%). Chemical sprays were the main form of pest and disease control reported by all farmers. The direct quantification sampling data revealed that 73.07% of the tomatoes were substandard at the farm level, with 47.92% and 25.15% categorized as medium-quality and poor-quality, respectively. The primary contributors to the losses were decay (39.92%), mechanical damage (31.32%), and blotchiness (27.99%). Postharvest losses were significantly higher under open-field production systems compared to closed tunnels. The fungi associated with decay were mainly Geotrichum, Fusarium spp., and Alternaria spp. These findings demonstrate the main drivers behind postharvest losses, which in turn highlight the critical need for intervention through training and support, including the use of postharvest loss reduction technologies to enhance food security.