Although many analysts recognize that team-level learning is reliant on the acquisition of learning content by individuals, very little research has examined individual-level learning during team training. In a sample of 70 teams (N = 380) that participated in a simulation-based team training setting designed to teach strategic decision-making, we examined how self-regulation during team training influenced the extent to which team members subsequently demonstrated individual mastery of the team training content. We also investigated the extent to which team characteristics moderated the relationships between self-regulation and learning outcomes. Multilevel mediation results indicated that self-efficacy fully mediated the effects of metacognition, or self-monitoring of learning, on individual declarative and procedural knowledge of team training content. The results also revealed that these individual-level relationships were moderated by the team context. In particular, a team’s overall performance and quality of cooperation amplified the positive effects of individual self-regulation. Implications for team training research and practice are discussed.