This systematic review is based on studies that explored school readiness and transition through play-based pedagogies in Early Childhood and Primary Education. Relevant literature involved global literature whose search was conducted by independent researchers following the keyword string, which included among others, stakeholders’ roles in school readiness, transition, and play-based pedagogies. The literature search was done from May to August 2022 following the Preferred Reporting Item for Systematic Review and Meta-Analysis Protocols (PRISMA). Twenty peer-reviewed studies were identified, appraised, and included in the review. Findings from international literature showed that teachers’ implementation of play-based pedagogy revealed a significant and positive relationship to all domains of children’s holistic development. Learner assessment for school readiness and transitioning from pre-primary to primary through play-based pedagogies included academic, social, and personal learning during periods of play. The types of play-based assessments for school readiness identified included: (1) withdrawal assessment, (2) observational assessment, (3) embedded assessment, (4) teacher questioning/interview, (5) Photographs/videos and (6) documentation walls. While literature showed a positive connection between parental involvement and a child’s readiness for school including successful transition from preprimary to primary school, there was limited evidence pointing specifically to the influence of parental involvement in play-based pedagogies for school transitioning.