The professional truck driver population is aging in Australia and internationally. However, there is currently a gap in knowledge related to the morbidity of workers in the transport industry. Understanding the health and wellbeing of workers employed in the transport industry should be a priority to ensure the appropriate allocation of resources to prevention and rehabilitation efforts. This study explored the landscape of work-related injury and disease in the Australian transport industry, by measuring injury and illness resulting in time loss in truck drivers by age group. The study used a population based, retrospective cohort study based on claim data collected from the National Dataset for Compensation-based Statistics in Australia. Analysis on a total of 120,742 accepted workers’ compensation claims was performed to characterize the distribution of workers’ compensation claims by four time periods (2004–2006, 2007–2009, 2010–2012, and 2013–2015), age groups, and jurisdictions. Three key findings were identified: the relative risk of workers’ compensation claims increased with age; older truck drivers (i.e., 65 years and over) did not have significantly higher rates of musculoskeletal injury (MSK) or fracture injuries, and; older truck drivers had a significantly larger proportion of neurological injury compared to younger age groups. The findings of this research support the need for context sensitive, multi-domain, interventions targeted at older truck drivers in order to both prevent work-related injury and disease and reduce the burden of disability once an injury or disease has occurred.