To successfully evolve, organizations should change at the same pace as the environment changes. It is particularly important when adapting and utilizing new media technology is a huge part of an organization’s success. Presently, media professionals in all industries including intercollegiate athletics are experiencing a significant change in their work environment due to the ever-changing nature of new media technology. In particular, media convergence, an integration of production by combining both old (e.g., television) and new media (e.g., the Internet), has been one of the most influential phenomena creating unexpected changes and complex dynamics in the current media industry. Nonetheless, what have been previously overlooked in sport communication literature are challenges generated by media convergence, which affects the nature of sport communication. This case study provides a scenario based on semi-fictitious information so that students can critically examine the dynamic nature as well as the effect of media convergence facing sport communication in intercollegiate sport. Further, the students are provided with an opportunity to practice decision-making skills to address the challenges stemming from media convergence. By doing so, discussion regarding media convergence in the context of intercollegiate sport could be better presented to relevant classroom discussion.