This study examined the relationship between learning readiness and academic performance of kindergarten pupils in Dolores I District, Eastern Samar, during the School Year 2023–2024. Using a descriptive–correlational research design, the study assessed pupils’ readiness at the beginning of the school year and their academic performance at the end of the year. A total enumeration of kindergarten pupils with complete records served as respondents. Data were gathered from standardized readiness assessment tools and official Kindergarten Progress Reports and were analyzed using descriptive statistics and Pearson’s correlation. Findings revealed that the pupils’ overall learning readiness was Approaching Ready, with Physical and Motor Development and Socio-emotional Development emerging as the strongest domains. Approaches to Learning was identified as the least developed domain, indicating challenges in attention, persistence, and task engagement. Academic performance was rated Developing, with stronger outcomes in socio-emotional and psychomotor skills and weaker performance in early literacy, early numeracy, and work habits. A strong, significant relationship was found between learning readiness and academic performance (r = 0.68, p = 0.001). Among the readiness domains, Approaches to Learning, Cognitive Development, and Language and Literacy Development showed the highest correlations with academic performance, indicating their strong predictive value. The study concludes that enhancing readiness—especially behavioral, cognitive, and language-related skills—is crucial in improving kindergarten achievement. It recommends strengthening early learning interventions, parental engagement, and developmentally appropriate instructional practices to support foundational learning in the district.