Using a nationally representative sample of 4,511 Singaporeans aged 55+ from the 2005 National Survey of Senior Citizens (NSSC), this paper examines gender differences in specific diseases, impairments, and disabilities, and computes health expectancies for these health dimensions. Results show that women have higher prevalence for hypertension, bone/joint, eye/vision, and walking problems, while heart diseases and stroke are more common among men, particularly at younger ages. At ages 75+, women have more disabilities related to basic activities of daily living (bathing, dressing, toileting, transferring, and feeding) than men. Health expectancies computations by the Sullivan method reveal that while women live longer than men, they can also expect more years of life both without and with diseases, impairments, and disabilities. At age 65, a larger proportion of women's remaining life is with hypertension, bone/joint problems, vision impairments, walking difficulties, and functional disabilities compared to same-aged men. The findings largely support the gender health-survival paradox found in Western countries--that women have higher morbidity rates despite longer life expectancy. The morbidity differences between men and women, however, vary depending on the particular health dimension and measure examined. Older women in Singapore tend to be advantaged in prevalence of diseases and disease-free life expectancy, but have more impairments and functional disabilities, and a larger proportion of remaining life with these difficulties compared to older men. Health policies and programs in Singapore will need to cater to these gender differences in specific health dimensions and measures.