It has been argued that ‘successful aging’ should be inclusive of a dynamic perspective that incorporates context, social influences, and social structure. Previous research has acknowledged that transitions in work and family life have implications for health and wellbeing. However, such transitions have typically been explored independently and there is a need for collective exploration. This systematic review of studies aimed to identify transitions that have been commonly investigated and synthesize the relationship between work and family-life transitions on health outcomes. Searches were conducted across five electronic databases: ASSIA, CINAHL, Medline, PsycINFO and Web of Science and 78 studies were included. Studies investigated bereavement (n = 22), employment (n = 21), parenthood (n = 20), marital (n = 10), or multiple (n = 5) transitions. It was found that the majority of health outcomes were mental health-related (n = 46), with a lack of evidence surrounding other health outcomes, including non-communicable diseases (n = 2), general/functional health (n = 3), multiple conditions (n = 16), and health behaviors (n = 11). The NIH Quality Assessment Tool was used to assess study quality. Studies were rated as good (n = 47), fair (n = 25) and poor (n = 6). It was identified that regardless of the specificity of the transition, many transitions resulted in a temporary decline in health. Such findings suggest that, according to a Life Course Theory approach, each life transition may have lasting implications that contribute to an individual’s overall developmental trajectory. Consequently, there is a need for studies of transitions and outcomes that focus on specific indicators of physical health or the inclusion of multidimensional instruments of health-related qualities.