INTRODUCTION: Patients with chronic diseases face difficulties when navigating the healthcare system. Using the Healthcare System Hassles Questionnaire (HSHQ) developed by Parchman et al, this study aimed to explore the degree of hassles faced by patients in primary care in Singapore and identify the characteristics associated with greater hassles. METHODS: A cross-sectional study was conducted on patients with chronic diseases at Hougang Polyclinic, Singapore, using the interviewer-administered HSHQ. The mean HSHQ score was compared with that reported by Parchman et al. The associations between the number of chronic diseases, demographic variables and healthcare hassles were assessed using multivariate linear logistic regression analysis. RESULTS: In total, 217 outpatients aged 21 years and above were enrolled. Their overall mean HSHQ score (4.77 ± 6.18) was significantly lower than that of patients in the study by Parchman et al (15.94 ± 14.23, p < 0.001). Patients with five or more chronic diseases scored 3.38 (95% confidence interval [CI] 0.11-6.65, p = 0.043) points higher than those with one chronic disease did. With each increasing year of age, the mean HSHQ score decreased by 0.17 (95% CI -0.26 to -0.08, p = 0.001) points. Patients with polytechnic/diploma/university education and higher scored 2.65 (95% CI 0.19-5.11, p = 0.035) points higher than those with primary education and lower did. CONCLUSION Patients in our population reported less hassles than those in the study by Parchman et al did. Increasing age and lower education level were associated with less hassles. Further analysis of the types of chronic diseases may yield new information about the association of healthcare hassles with the number and types of chronic diseases.