INTRODUCTION: This study aims to examine the factors associated with self-reported hearing disability and early reduction in disability after first-time hearing aid (HA) fitting in Singapore. METHODS: Retrospective record review of 1,068 subjects issued with HAs at a tertiary hospital from 2001 to 2013. RESULTS: Subjects reporting ≥5 disabilities reduced from 90% to 24% after HA fitting. 'Difficulty hearing in noise' was the commonest disability before and after HA fitting, while 'needs to increase volume of TV/radio' was the disability with most improvement after fitting. In multivariable models, having worse pure tone audiometry (PTA) thresholds of the better hearing ear and being ethnically Chinese were associated with subjects reporting more hearing disabilities. A higher proportion of subjects reported a reduction rather than an absence of disability after HA fitting. In multivariable models, daily HA usage for ≥4 hours, sensorineural hearing loss (HL) and worse PTA thresholds of the better hearing ear were associated with reduction in more disabilities after HA fitting. CONCLUSION Hearing disability is high among first-time HA users in Singapore. Ethnicity and PTA thresholds were associated with self-reported hearing disability. After HA fitting, higher daily HA usage, sensorineural HL, and worse PTA thresholds of the better hearing ear were associated with early reduction in disability. Patient counselling on the benefits of HL rehabilitation could focus on hearing disability rather than PTA thresholds. The management of patients' expectations could focus on reducing rather than eliminating disability.