The current research was designed to further comprehend the nature of the relationship between small and medium-sized sponsoring enterprises and their affiliated sport organizations. In order to achieve this purpose, the research has involved some of the major sponsors of Italian rugby teams that participate in the Championship that has limited media exposure. Using semi-structured interviews the study focused on understanding what managers think of sponsorship and exploring the underlying reasons in a small business decision to sponsor a sport team with poor or limited media visibility. Results show that the involvement of local firms in the city’s activities is very important. When sponsors exploit these forms of sponsorship as a way of helping the local community, then they seem to adopt these sponsorships to reach an effective outcome in terms of brand awareness and return on investment. Conclusions are discussed and recommendations are offered.