The dynamic nature of destination image (DI) has been widely recognized. However, studies using longitudinal repeated measures to trace image change over time are limited. The first author and her colleagues have examined the structural stability of the DI held by a group of sport tourists over a 10-month interval after attending a marathon event, by adopting a tripartite attitudinal perspective. Their study revealed a significant decay in the affective DI and conative DI, but not in the cognitive DI. The current paper serves as an extended study to find out: first, will the decay of affective DI and conative DI held by sport tourists persist over time? Second, what factors will influence sport tourists’ DI decay over time? Three online surveys were conducted to monitor the post-event DI change of 50 non-local marathon participants over 20 months after returning from the host destination. GLM Repeated Measures Analyses revealed that the post-event affective DI significantly declined in the first 10 months, but then rebounded in the following 10 months, while the conative DI showed a continuous decline over the 20 months. Furthermore, the change pattern of conative DI was moderated by the psychological connection level that a sport tourist has with the host destination. Relevant theoretical and managerial implications are addressed to provide insights for both researchers and practitioners.