The practice of workplace learning is important for small and medium enterprises (SMEs) to stay competitive in the face of today’s environmental pressures from globalisation, competition, technological advancement and the knowledge economy. However, firm characteristics such as limited internal resources and capabilities are factors that affect how they practise workplace learning at any given point in time. According to organisational life cycle (OLC) theory, during the firm’s growth from inception, to high-growth, to maturity, the internal resources and capabilities of the firm develop. The literature has discussed workplace learning and the organisational life cycle separately, and little is known about how they are related. This study attempts to connect the workplace learning practices in SMEs and the organisational life cycle to understand how they practice workplace learning at different life-cycle stages. The research reports on a case study of 30 Hong Kong SMEs at different life-cycle stages (11 at inception, 10 at high-growth and 9 at maturity). Two consecutive phases of data collection are involved. Phase I identifies the life-cycle stage of the firm through theoretical sampling with an OLC questionnaire. Phase II adopts a mixed methods design to explore the workplace learning practices (categorised by learning levels) in those SMEs at each life-cycle stage through the online Learning Practices Questionnaire (LPQ), as well as semi-structured interviews with 4 SMEs identified at each stage through snowball sampling with data gathered until data saturation was reached. Both quantitative and qualitative results lend support to each other. Results of this study show that the levels of workplace learning practised by SMEs are varied in importance between life-cycle stages (except inter-organisational learning which is common to all stages). Four major findings emerge: (1) The individual level of workplace learning is important at all life-cycle stages but most important at inception. (2) The group level of workplace learning is more important at high-growth than it is at maturity. (3) The organisational level of workplace learning is more important at high-growth and maturity than it is at inception. (4) The inter-organisational level of workplace learning is high at all life-cycle stages and there is no significant difference between stages. To conclude, this study has established a connection between the workplace learning practices in SMEs and the organisational life cycle, providing owner/managers with a better understanding of how the firm’s development relates to their workplace learning strategies.