Background: The use of facemasks is a key preventive measure against the COVID-19 pandemic. Wearing a facemask for long periods can cause maskassociated dry eyes. This study explored the prevalence of facemask-related dry eyes (MADE) and associated factors. Methods: This study was crosssectional, carried out on healthcare workers in Primary Healthcare Centers (PHCs) in Jeddah, Saudi Arabia. Descriptive statistics were performed. Chi-Square was used to evaluate the association between determinant and outcome variables. P-value < 0.05 was considered for significance. Regression analysis was applied to identify the contribution of independent factors to the outcomes. Results: Our study got a 91% response rate. The prevalence of mask-associated dry eyes was 70.9%. Participants aged 31-40 years had almost three times more likelihood to develop MADE (OR: 2.98; 95% CI: 1.493-5.947), and those aged 41-50 years had 2.54 odds of developing MADE (OR: 2.54; 95% CI: 1.090-5.924). Time spent on digital screens (> 4 hours) was 2.38 times more associated with MADE, while radiology staff, medical specialists, medical consultants and managerial team were less likely (OR=0.097, OR= 0.257, OR=0.222, and OR=0.290, respectively) of developing MADE. There was no statistically significant association of MADE with pre-existing eye problems (p>0.05). Conclusion: The prevalence of mask-associated dry eyes was high.Increased age and screen time were significant independent factors associated with risks for MADE, while being a radiology staff and managerial team member, medical specialists, and medical consultants were associated with lower risks for MADE than other healthcare workers.