Background: Pretend play is a form of play that involves nonliteral actions. There are limited studies reporting the developmental trends of pretend play behaviours of typically developing pre-schoolers. This knowledge would be beneficial in the early identification of deviations in pre-schoolers who have or are at risk of developing developmental disabilities. Aim: The present study aimed to describe the developmental trends in pretend play skills across different age groups of pre-schoolers. The study also aimed to understand the differential patterns in pretend play observed across the Free Play and Structured Toy Play scenarios. Setting: This study was conducted on pre-schoolers in a classroom of the school. Method: The study followed a cross-sectional study design. Forty-eight participants were recruited for the study and were divided into four groups. A video recording of the child's pretend play skills was recorded using a Sony-HDRCX405 camcorder in Free Play and Structured Toy Play scenarios. The recorded video was coded and analysed for the occurrence of pretend play skills using the Play in Early Childhood Evaluation System (PIECES) coding scheme. Results: The study results depict a developmental trend in the occurrences of pretend play skills in pre-schoolers. It also emphasises the importance of amalgamation of Structured Toy Play and Free Play scenarios for the child's holistic development because of the unique benefits of each scenario. Conclusion: The study findings could help in the formulation of Individualised Education Programme objectives for typically developing children and children with developmental disabilities involving play, thus enabling these children experience normalised, contextually pertinent experiences like their peers.