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The relationship between homelessness, violence and crime is a complex one, with the inclination to criminalise often outweighing interest to understand and acknowledge patterns of victimisation within academic discourse and related sectors. This dominant perspective is particularly evident within the South African context, where scant and small-scaled research efforts characterise the exploration of victimisation of individuals experiencing homelessness, resulting in the dearth of local research and a large contextual gap. Consequently, the lack of understanding drives the under-prioritisation of their vulnerability to victimisation in mainstream legislation, policy and subsequent intervention measures. The paper presents the findings of a study which employed a quantitative, novel two-pronged approach, using a questionnaire (survey) for data collection, to explore the experiences of victimisation and determine the immediate service needs of people experiencing homelessness. Within the context of sizeable and rather diverse sample (n = 150), the findings revealed distinct features characterised by unique pathways into homelessness and the prevalence of dynamic risk factors which could potentially influence their vulnerability to victimisation. Central to the objective study, the analysis revealed that a significant proportion of respondents had experienced victimisation (n = 89; 59.7%), with a plethora of personal accounts related to their immediate service needs and the persistent impact of systemic barriers as their navigate life. Furthermore, the findings provide a holistic and updated understanding of the complex relationship between homelessness and victimisation, with significant considerations for policy and practice.