This paper aims to identify two different knowledge management (KM) systems and their underlying capabilities by accounting for two contextual factors: organisational structures and type of knowledge. Specifically, it seeks to explore how two different organisational structures (mechanistic and organic) shape the way explicit and tacit knowledge is shared, created, and learned. The paper uses a case-based approach of two sports teams as archetypal contexts to inform management research. Findings suggest that a mechanistic structure (American football) emphasises explicit knowledge for sharing of specific directives, centralised, incremental knowledge creation, and organisational learning through memorisation and repetitious actions. In an organic structure (ice hockey), sharing of tacit knowledge, decentralised novel knowledge creation, and organisational learning through empowered experiential learning episodes are emphasised. Findings illustrate the importance of accounting for organisational structures and knowledge needed for different KM systems geared towards efficiency and routine work, and flexibility and non-routine work.