Objective: This study identified associations between chronic diseases (diabetes, asthma, depression, and arthritis) and workforce participation patterns with a gendered perspective. Method: We used data from 1,261 middle-aged participants of the Australian Life Histories and Health (LHH) Survey, aged 60 to 64 years in 2011. Latent class analysis identified dominant workforce patterns and associations between chronic diseases and these patterns were explored by multinomial regression models. Results: Diabetes, asthma, depression, and arthritis were less prevalent in men and women in class "mostly full-time work," compared with other workforce patterns. The odds of "mostly full-time work" were lower for men reporting depression or arthritis, whereas among women, depression was associated with "increasing part-time work" after adjusting early and adult life factors. Discussion: The results strengthen the importance of gender focused policies aimed to promote and preserve health of young and middle-aged workers, and creating supportive environment for those with chronic health issues over the life course.