The health and performance of the small- and medium-sized enterprise (SME) sector is crucial to regional and national economies of most developed countries (Jones, Macpherson and Thorpe, 2010; Thorpe, Cope, Ram and Pedler, 2009). In recognition of this, Higher Education Institutions (HEIs) have been supported through government policy to provide training programmes for SMEs aimed at developing a higher level of skills that will support small business growth (European Commission, 2003; Lambert Review, 2003; Leitch Review of Skills, 2006; DIUS, 2007, 2008; Zhang and Hamilton, 2010). In this paper we explore the relationship between entrepreneurship education and regional development by examining a programme delivered by a higher education institution for growth-oriented small business owners. We concern ourselves with addressing the overarching questions: What is the impact of HEI and SME engagement on entrepreneurship education? And How does HEI/SME engagement impact on a regional economy? To deal with these questions a qualitative approach to the research was adopted to examine the situations of five SME owner/managers over a five year period. Findings show that entrepreneurship education delivered a range of economic benefits to SMEs and the region. Moreover, through engaging owner/managers have the opportunity to interact with others and this supports the growth and development of the business.