Play is a universal code, which mirrors the all-round development of a child. Play development reflects the emergence of early cognitive skills in children. The current study profiles the developmental trends of different types of play during the free and structured play scenario in South India. The sample included 48 pre-school children, aged between 3.6 to 5.6 years. Children’s play was recorded in two scenarios, which included free Play (spontaneous Play without any restrictions) and structured toy play (restriction of toy usage limited to the four types of toys provided by investigator), in the classroom settings. The data was analysed using the coding scheme that was adapted by combining two existing standardised play scales i.e. Play Observation Scale and Play in Early Childhood Evaluation System. In the coding scheme, play types were grouped under three domains which were Functional Play, Social Play, and Cognitive Play. Cognitive play was further divided into two domains that are Simple pretend play (SPP) and Complex pretend Play (CPP) which has the subtypes adapted from Play in Early Childhood Evaluation System. The results revealed that the occurrence of play type was higher in the free play scenario and reduced in the structured toy play scenario. A developmental trend was observed in free play over structured toy play among children. The findings would be helpful in planning play-based counselling/intervention strategies for children and create awareness to teachers about the various developmental patterns of play types.