Purpose: This article explores the evolution of international bonds between Middlesbrough in the north east of England and North Korea arising from the participation of the North Korean men’s football team at the 1966 FIFA World Cup. Shedding new light on the origins of this example of sporting diplomacy, this research seeks to understand the dynamics of international relations enacted at a local level and highlights the role of key individuals and institutions in facilitating this connection between the town and North Korea into the twenty-first century. Design, Methodology, Approach: Beginning with an assessment of early interactions between Middlesbrough and North Korea, this paper analyses the way in which the relationship has been articulated and developed across several decades. Drawing upon local authority archives, historic newspaper collections, oral history and private collections, this study brings together hitherto underexplored resources, including North Korean diplomatic correspondence and interviews with the footballers of 1966, to deconstruct the multi-layered mechanisms, meanings and motivations that underpin the Middlesbrough-Pyongyang relationship. Findings: Focusing chiefly on the role of British agency in North Korea-UK interactions, this research reveals the combination of local sporting conditions, international relations and individual and institution engagement in constructing bonds between Middlesbrough and North Korea since 1966. In doing so, the article draws out some of the peculiar local, economic and political factors that have shaped and nurtured the sporting, pseudo-diplomatic connections between Pyongyang and Teesside. Practical Implications: This study highlights the important role that sport can play in harnessing new international interactions and understandings between peoples from different cultural and political systems. The power of football and bonds created at a local level (in this case Middlesbrough) to help nurture international diplomatic relations and embrace common transnational interests is also considered, as are the limitations of what might be considered a strand or extension of sports diplomacy. Originality, Value: Expanding beyond the existing literature on sports diplomacy, mega events and official interactions between North Korea and the UK, this article utilises hitherto unpublished historical documentation and new oral testimony to bring a new perspective on the benefits and challenges posed by interactions across international borders facilitated by sport, both at the FIFA World Cup in 1966 and in recent decades