Introduction: Older taxi drivers in Singapore face mandatory retirement at 73 years of age, often marked by the simultaneous loss of the worker and driver roles. The Driver Retirement Program was developed as an intervention to support this transition. Method: A pre- and post-experimental design was conducted with retired 73-year-old, male taxi drivers (n ¼ 15) to investigate the hypotheses: (i) the Driver Retirement Program would increase activity participation (e.g. time use) and wellbeing (e.g. mood) outcomes at immediate post-intervention and (ii) maintain these changes at 3 months’ follow-up. Non-parametric tests were used to compare changes between (i) pre- and post-intervention and (ii) 3 months follow-up to post-intervention. Participants’ feedback on the Driver Retirement Program was obtained using a semi-structured questionnaire. Results: The Driver Retirement Program significantly improved mood, self-efficacy and satisfaction with individualised goals at post-intervention and maintained these changes at 3 months’ follow-up. A significant decrease in time spent alone was found at follow-up compared with post-intervention. Participants rated high satisfaction with the Driver Retirement Program but also recommended a shorter programme without compulsory group sessions. Conclusion: The Driver Retirement Program was useful to support some aspects of work and driver retirement transition. Further work to enhance sensitivity to cultural and gender issues is indicated.