This study investigated the relationship between play-based learning strategies and cognitive readiness, particularly attention span—among early learners in Montessori schools within Lagler Local Government Area, Ibadan, Oyo State. Guided by Piaget’s Cognitive Development Theory and Vygotsky’s Sociocultural Theory, the study employed a descriptive survey design involving early learners and their teachers across selected Montessori schools. Data were collected using a teacher questionnaire and an observation checklist, and analyzed using descriptive statistics and the Pearson Product Moment Correlation Coefficient (PPMC). Findings showed that storytelling emerged as the most commonly adopted play-based learning strategy, followed by outdoor/free play and puzzle-solving activities. However, classroom observations revealed a stronger presence of free play and music/movement activities, suggesting some variation between teacher-stated practices and actual implementation. Learners generally demonstrated the ability to sustain attention for more than five minutes and follow instructions effectively, indicating that structured play promotes focus, engagement, and cognitive readiness. Correlation analysis revealed significant positive relationships between all play-based learning strategies and cognitive readiness, with construction play showing the strongest association, followed by outdoor/free play and role/dramatic play. These results highlight that although storytelling is the most frequently used strategy, hands-on and exploratory forms of play show greater influence on learners’ attention and overall cognitive development. The study concludes that a balanced integration of diverse play-based strategies, supported by adequate learning materials and intentional teacher facilitation, enhances learners’ cognitive readiness for formal learning. It recommends improved teacher training, better resourcing of play environments, and the institutionalization of structured play routines to maximize the cognitive benefits inherent in Montessori pedagogy.