This study investigated the cross-lagged associations between work engagement and burnout, and life satisfaction and depressive symptoms, their demands (i.e., workload) and resources (i.e., servant leadership, self-efficacy, resilience) and relationships with occupational health outcomes (i.e., recovery, number of mental health diagnoses, workaholism). This study is a part of an ongoing Occupational Health Study in which 1 415 employees (586 men, 829 women) were followed twice during two years 2011–12 through their occupational health services. The participants filled in a questionnaire on their work engagement, burnout symptoms, well-being, personal and work environmental resources and demands, and occupational health. The results showed that spillover existed, in particular, from work engagement to depressive symptoms (negatively), and to life satisfaction (positively) and from depressive symptoms to work engagement (negatively), and to burnout (positively). Work engagement was also negatively associated with work burnout, and depressive symptoms were negatively associated with life satisfaction. Moreover, servant leadership was positively associated with work engagement, which, in turn, was positively associated with high life satisfaction and recovery, and negatively associated with work burnout and depressive symptoms. High workload, in turn, was positively associated with burnout and depressive symptoms, which, in turn, were further positively associated with increased mental health diagnoses, and negatively associated with recovery.