The rail industry in Australia screens workers for probable obstructive sleep apnea (OSA) due to known safety risks. However, existing criteria to trigger screening only identify a small proportion of workers with OSA. The current study sought to examine the relationship between OSA risk and rail incidents in real-world data from Australian train drivers, and conducted a proof of concept analysis to determine whether more conservative screening criteria are justified. Health assessment (2016–2018) and subsequent rail incident data (2016–2020) were collected from two passenger rail service providers. Predictors included OSA status (confirmed no OSA with a sleep study, controlled OSA, unknown OSA [no recorded sleep assessment data] and confirmed OSA with no indication of treatment); OSA risk according to the current Standard, and OSA risk according to more conservative clinical markers (BMI threshold and cardiometabolic burden). Coded rail safety incidents involving the train driver were included. Data were analysed using zero-inflated negative binomial models to account for over-dispersion with high 0 counts, and rail safety incidents are reported using Incidence Risk Ratios (IRRs). A total of 751 train drivers, typically middle-aged, overweight to obese and mostly men, were included in analyses. There were 43 (5.7%) drivers with confirmed OSA, 62 (8.2%) with controlled OSA, 13 (1.7%) with confirmed no OSA and 633 (84.4%) drivers with unknown OSA. Of the 633 train drivers with unknown OSA status, 21 (3.3%) met ‘at risk’ criteria for OSA according to the Standard, and incidents were 61% greater (IRR: 1.61, 95% Confidence Interval (CI) 1.02–2.56) in the years following their health assessment compared to drivers who did not meet ‘at risk’ criteria. A more conservative OSA risk status using lower BMI threshold and cardiometabolic burden identified an additional 30 ‘at risk’ train drivers who had 46% greater incidents compared to drivers who did not meet risk criteria (IRR (95% CI) 1.46 (1.00–2.13)). Our more conservative OSA risk criteria identified more workers, with greater prospective incidents. These findings suggest that existing validated tools could be considered in future iterations of the Standard in order to more sensitively screen for OSA.