This study investigated Hong Kong and German children’s perceptions of play and learning and their relationships. Forty-eight children (24 German and 24 Chinese) playing and learning in the classroom were observed and videotaped for five consecutive days. They were interviewed 3 times about their kindergarten experiences by using free- and cue-recall questions. It is found that the Hong Kong children remembered more academic learning activities, whereas the German children remembered more play events. Most of the Hong Kong children recalled academic learning content, whereas the German children associated learning with play. The findings showed that children’s understandings of the relationship between play and learning varied with their classroom contexts. These results suggest that children’s perspectives on play and learning should be taken into account by advocating a play-based pedagogy approach or integrating more learning elements into a play-oriented curriculum. The implications for policy and pedagogy are discussed.