From the beginning of civilisation, money has been considered a fundamental aspect in our day-to-day functioning. Therefore, acquiring and developing money handling skills is important for all human beings. Similarly, money skills are an integral aspect of living for individuals with intellectual disabilities such as Down syndrome. Gaining money skills for those with Down syndrome will help enable them to lead an independent life, participate in community activities and improve their quality of life. Out of the many teaching strategies adapted to teach money skills to individuals with intellectual disabilities, the Next Dollar Strategy has been found to be one of the most successful. In addition, video modelling (VM) and video self-modelling (VSM) are widely used instructional procedures which have been effective in teaching various skills to individuals with intellectual disabilities. The aim of the present study was to investigate the effects of teaching the Next Dollar Strategy to 6 adolescents/young adults with Down syndrome via VM and VSM using a non-current multiple baseline design yoked across participants and a twelve step purchasing goods procedure. The results of the study found that both VM and VSM interventions assisted in increasing the purchasing skills acquisition for all 6 participants. The VM intervention was more effective in teaching the Next Dollar Strategy compared to the VSM intervention. However, only one participant of the 6 was able to master the Next Dollar Strategy and maintain it through the follow-up and generalisation phases. From this small study, the findings suggest that teaching the Next Dollar Strategy to individuals with Down syndrome by using VM or VSM appears to be not the most effective intervention strategy.