This research determined the numeracy skills of Grade Two learners in Sta. Cruz South District, Division of Davao del Sur, to support the formulation of a contextualized mathematics program. Using a non-experimental descriptive survey design, the study involved 400 learners who completed a mathematics test developed by the researcher. The assessment focused on three core skill areas: verbal counting, numerical operations, and problem-solving. Post-test results showed significant improvement from pre-test scores, with learners reaching a “Satisfactory” level in verbal counting and numerical skills, and a “Very Satisfactory” level in problem-solving. Analysis also revealed statistically significant differences in numeracy performance based on gender and school classification (urban vs. rural), highlighting the role of contextual variables in early mathematics learning. The study was anchored on Piaget’s Cognitive Development Theory and Constructivist Learning Theory, emphasizing hands-on and meaningful learning experiences. Based on the findings, a contextualized mathematics program was designed to better address the learners’ needs. The study recommended that educational leaders prioritize teacher training, inclusive instructional practices, and parent engagement to strengthen early numeracy foundations.