In an attempt to integrate research on stress coping and research on psychological well-being, we conducted longitudinal and disaggregated analyses of the relationships between leisure-related constructs (i.e., level of leisure participation and the importance of leisure goals) and psychological well-being for groups of individuals classified by gender and life events (i.e., chronic health problems and life transitions). Using two surveys on well-being in Canada, we found that (a) overall, the participants showed relative stability or little change in psychological well-being and leisure-related variables, (b) some life events (e.g., becoming widowed for women and becoming unemployed for men) had more detrimental impacts on psychological well-being than did others; (c) increased importance placed on leisure goals enhanced positive psychological well being for women who had become homemakers after having been employed, men who had experienced recent or long-term illnesses, and men who had married; (d) increased importance placed on leisure goals reduced negative psychological well-being for men who had become employed after having been unemployed; (e) results showed a stronger effect of change in leisure goals than of change in level of leisure participation on wellbeing; (f) several reciprocal relationships were supported, demonstrating that leisure can be both a cause and an effect of psychological well-being; and (g) some gender differences were shown in some indicators, the relationships between them, or both.