Despite the popularity of web-based dietary interventions, there are few evidence-based, practical guidelines that help human–computer interaction (HCI) practitioners design new dietary intervention systems. We suspect that a lack of such guidelines is partly due to a chasm between two major research domains, healthcare and HCI. We believe that technologies developed in HCI are not used and evaluated by healthcare researchers, so we fail to accumulate experiences to develop guidelines. To assess the gap, we carefully selected 86 papers that employed and evaluated various web-based dietary interventions in both fields and analyzed general characteristics, behavior change strategies, intervention media, and research outcomes used in each paper. Through this review, we reaffirmed our belief about the discrepancies between healthcare and HCI, and additional findings helped us offer some suggestions to close the gap. We also identified several interesting patterns among behavior change strategies, intervention media, and outcomes that provide potential topics for future research.