<b><i>Introduction:</i></b> Recent evidence suggests that poor sleep is a risk factor that contributes to the development of Alzheimer’s disease (AD). Most studies have focused on short-term effects of sleep deprivation on cognitive function, whereas longitudinal studies are limited to self-reported sleep and the risk of later-life dementia. Because sleep loss could be an early manifestation of neurodegenerative disease, reverse causality in these studies cannot be excluded. <b><i>Objective:</i></b> In this explorative, observational study, we investigated the effects of extended periods of extrinsically (work-related) caused sleep loss on later-life cognitive function, early dementia symptoms, and current sleep quality. <b><i>Methods:</i></b> We approached a community of retired male maritime pilots (approx. <i>n</i> = 500) through a newsletter. We investigated 50 respondents (mean age 71.7 years ± 7.7), with a history of &#x3e;25 years of work on irregular schedules, which resulted in extended periods of sleep loss. Validated questionnaires on cognitive complaints (Cognitive Failure Questionnaire [CFQ]), early dementia symptoms (Early Dementia Questionnaire [EDQ]), current sleep quality (Pittsburgh Sleep Quality Index [PSQI] and sleep-wake diaries), quality of life (QoL, EQ-5D), and mood (Hospital Anxiety and Depression Scale [HADS]) were administered by a single investigator (J.T.), who also completed an observer rating of cognitive function. <b><i>Results:</i></b> Scores on the CFQ, EDQ, PSQI, EQ-5D, and HADS were within normal ranges adjusted for age, sex, and education. The observer rating was not indicative of cognitive decline. <b><i>Conclusion:</i></b> We found no evidence that long-term exposure to work-related sleep loss had resulted in cognitive decline or early dementia symptoms in this sample of retired maritime pilots.