Driver sleepiness is a prevalent phenomenon among professional drivers working unconventional and irregular hours. For compromising occupational and traffic safety, sleepiness has become one of the major conundrums of road transportation. To further elucidate the phenomenon, an on-road study canvassing the under-explored relationship between working hours and sleepiness, sleep, and use of sleepiness countermeasures during and outside statutory rest breaks was conducted. Testing the association between the outcomes and working hours, generalized estimating equations models were fitted on a data collected from 54 long-haul truck drivers (mean 38.1±10.5 years, one female) volunteering in the 2-week study. Unobtrusive data-collection methods applied under naturalistic working and shift conditions included the Karolinska Sleepiness Scale (KSS) measuring sleepiness, a combination of actigraphy and sleep-log measuring sleep, and self-report questionnaire items incorporated into the sleep-log measuring the use of sleepiness countermeasures during and outside statutory rest breaks. Drivers’ working hours were categorized into first and consecutive night, morning and day/evening shifts based on shift timing. The results reveal severe sleepiness (KSS≥7) was most prevalent on the first night (37.8%) and least on the morning (10.0%) shifts. Drivers slept reasonably well prior to duty hours, with main sleep being longest prior to the first night (total sleep time 7:21) and shortest prior to the morning (total sleep time 5:43) shifts. The proportion of shifts whereby drivers reported using at least one sleepiness countermeasure outside statutory rest breaks was approximately 22% units greater for the night than the non-night shifts. Compared to the day/evening shifts, the odds of severe sleepiness were greater only on the first night shifts (OR 6.4–9.1 with 95% confidence intervals, depending on the statistical model), the odds of insufficient daily sleep were higher especially prior to the consecutive night shifts (OR 3.5 with 95% confidence intervals), and the odds of using efficient sleepiness countermeasures outside statutory rest breaks were greater on the first as well as consecutive night shifts (OR 4.0–4.6 with 95% confidence intervals). No statistically significant association was found between shift type and use of efficient sleepiness countermeasures during statutory rest breaks. In all, the findings demonstrate marked differences in the occurrence of severe sleepiness at the wheel, sleep preceding duty hours, and the use of sleepiness countermeasures between different shift types. In addition, although drivers slept reasonably well in connection with different shift types, the findings imply there is still room for improvement in alertness management among this group of employees.