Using a drawing-based research approach, this qualitative study explored in-service infant teachers’ reflections on their play experiences and ways of supporting and scaffolding infants’ play at a childcare center in Korea. The participants engaged in a drawing task that illustrated their reflections and memories of their play. They then discussed their drawings by, answering semi-structured interview questions. An analysis of the images and comments depicted in the activity and shared in the interview revealed that participants recalled social and imaginative childhood play memories using natural objects and playing childhood games outdoors. Everyday activities were also regarded as play among the participants, and play activities changed depending on interests, personality, age, and societal situation, such as the Coronavirus pandemic. The findings revealed that infant teachers’ interests and preferences influenced their decisions to structure and scaffold or discourage certain play activities in the classroom. Through play, both infants and infant teachers shared positive affect and playfulness. This study suggests a crucial need for early childhood professionals to self-reflect to understand their preferences and play experiences, contemplate how their preferences and experiences impact their teaching practice, and meaningfully integrate play activities in their classrooms.