Research question: Small-scale sports events provide commercial opportunities for regional communities, and yet research suggests that local commercial organisations are sometimes reticent to engage with sport event organisations to leverage benefits. This paper examines variation in business engagement with sport events and identifies determinants to sport event leverage that are previously unrecognised in the academic literature. Research methods: Using a multiple case study approach in three regions of eastern Australia, this research examines reactions to a sport event within each respective host business community. The multiple cases allow comparison of results across regions, using a mixed method strategy of personal interviews, observation and document analysis. Results and findings: The main findings reveal six key determinants of organisational engagement with regional sport events being: event cooperation, tourism dependency, business size, promotional strategy, strategic direction and skills and knowledge. These key determinants are explored to create a framework for future research in this area, and further contribute to the field of sport leverage research, with particular importance to sport events. Implications: The barriers to the development of strategies to maximise event leverage are identified and discussed, and in so doing implications for improving business relationships with sport events are explored. These implications are relevant to managing impacts upon businesses, visitors, and event and regional destinations.