Web-based ticketing has become a prominent source of revenue for sports organizations. Sports fans today are increasingly searching for and purchasing tickets through the Internet. To increase the potential online ticket sales, sports organizations should take the ticketing website as an effective sales tool seriously and provide customers clear ticket information as well as simple and interactive ticket purchasing processes to fulfill their demands. However, little is known about the underlying extent of the ticketing website navigational structure and interactive features. To fill the gap, at least in part, this dissertation employed the proposition of the modality-agency-interactivity-navigability (MAIN) model and the theory of interactive media effects (TIME) as the theoretical basis in a setting of the sports online ticketing. The MAIN model and the TIME model explore the influence of technological affordances (e.g., modality, agency, navigability, and interactivity) of digital media on individuals’ evaluations and perceptions. In the current study, a 2 (navigability: complex vs. simple) × 2 (interactivity: high interactivity vs. no interactivity) between-subjects factorial designed online experiment was conducted to investigate the influence of website navigability and interactivity on customers’ experiences, attitudes toward the website, and ticket purchasing intentions. Moreover, the mediating effect of user experience (UX) and attitude toward the website was also examined. The results first indicated that navigability and interactivity of the ticketing website had significant main effects on participants’ UX and attitudes toward the website respectively. When a ticketing website provided necessary ticket information and links directly with fewer clicks (i.e., simple navigability design), participants generated more positive UX and attitudes toward it than those who browsed the website with complex navigability structure. Similarly, if a ticketing website utilized some interactive functions such as 360° relative seat section viewing, users would perceived more active control over the website and therefore expressed more positive UX and attitudes toward it than those who used the website with no interactive feature. Next, the results suggested that UX is not only a measurement tool, but also an important mediator between the technological affordances (i.e., navigability and interactivity) of the interactive digital media and users. Overall, two main UX constructs, pragmatic UX and hedonic UX, were identified. Under the premise that navigability had a direct effect on both UX and interactivity had a direct effect on hedonic UX, both UX were recognized to have direct and/or indirect (via attitude toward the website) influence on participants’ ticket purchasing intentions. The findings revealed some insights into the fields of sport marketing, user experience, interactive digital media effect, and consumer research theoretically and practically. This dissertation, as one of the pilot studies, advances the current understanding of UX, the MAIN model, and the TIME model by applying them to the sports online ticketing setting and supporting their feasibilities. In addition, this dissertation provides a practical suggestion regarding online ticketing design and attribute. It is expected that the findings from this dissertation can supplement some knowledge of the academia and the sports industry.