Background: Shift work is a workschedule, since industrial era and some employees work in shift. It causes a desynchronization of the biological clock with consequences on sleep amount and quality, such as insomnia and easy fatigue. Obstructive sleep apnea (OSA) is one of the sleep problems that are getting more and more attention, but studies on the association between shift work and OSA were rare. Herein, we aimed to conduct a systematic review and meta-analysis to investigate the association between shift work and possible OSA. Methods: This study was conducted according to Preferred Reporting Items for Systematic Reviews and Meta-Analyses guidelines. We queried PubMed, Embase, and Web of Science databases using a related set of keywords. The inclusion criteria were as follows: (1) participants were adult employees hired by a company or organization; (2) exposure was shift work; and (3) outcome was possible OSA according to examination or assessment. Results: We included six studies in the systematic review and five studies were selected for further meta-analysis. A random-effects model showed an association of shift work with a small, non-significant increase in possible OSA cases (pooled prevalence relative risk = 1.05; 95% CI 0.85–1.30; p = 0.65). This association occurred in both healthcare and non-healthcare workers group. Conclusion: The association between shift work and possible OSA remains inconclusive and could be small if not negligible. Future studies should assess the association between specific work schedules and specific OSA definitions. Trial registration number: PROSPERO ID: CRD42020156837