Events are increasingly relied upon for destination development within cities through the realisation of event legacies. Yet event legacy research suggests that positive outcomes are not guaranteed, with negative effects often the case. The leveraging of event-led strategies has been suggested as a more sustainable approach. However, there has been limited research in this area. This qualitative case study investigates the intersection between events and homelessness within the context of an eventful city. In 2017, two major events that form part of Melbourne's events portfolio, the Australian Open and White Night, were staged amidst a backdrop of increasing homelessness in the city. Empirical data for this case study has been collected using three methods. First, active participant observation at White Night 2017 was undertaken to consider the way in which the issue of homelessness may have impacted upon, or been impacted by, the event. Second, an interview with the event's state government owner took place to develop an understanding of connections between major events and homelessness. Finally, media reports and documentation from local government were textually analysed to provide context for the way homelessness is presented within the city. The findings suggest that marginalised groups may both affect and be affected by events, and that the tight rotation of events within an eventful city may have an influence upon serious social issues such as homelessness.