An individual’s previous work experience may be an important factor in relation to safety behaviour. It is not uncommon to find work experience used as a criterion in a job advertisement, a hurdle during the selection process, and/or used as a gauge of a new employee’s training or induction requirements. The aim of this study was to examine six different measures of work experience, and the relationship between previous experience and safety. Six different measures of work experience were assessed on their ability to predict similarity between past job experience and future requirements of a job. The results showed that measuring work experience by identifying the total number of organisations and work groups or teams a target job has been performed in are good predictors of similarity between past job experience and future requirements of a job. The results also showed that participants who did not report an accident in their current job had larger similarity ratings between past and present experience in comparison to participants who did report an accident in their current job. The results are discussed in terms of safety and the practical implications for organisations measuring work experience during the hiring process.