This phenomenological study unfolded the views of teachers in assessing a child’s readiness for kindergarten based on age and skills. The narratives reflected the lived experiences, challenges, coping mechanisms and insights of the kindergarten teachers. There were eight (8) teacher-participants who have experiences kindergarten assessment, and they are purposively selected as informants. The data gathering of information in this phenomenological inquiry had employed in-depth interview of participants through virtual conference and limited face-to-face subsequently observing strict compliance of standard health protocol. Using thematic analysis, the views of the teachers in assessing a child’s readiness for kindergarten based on age and skills were as follows: Diverse Developmental Levels, Social and Emotional Variances, and Language Development Evaluation. On the coping mechanisms they employed to address challenges, the following were the themes and findings of the study: Adaptability to Individual Needs, Professional Development and The importance of observation. Lastly, the following were the insights drawn from the findings of the study: Data-Informed Decision Making and Parental Involvement Strategies. The goal of this study was to understand the experiences of teachers in terms of assessing school readiness based on age and skills. The new knowledge drawn from this study is noteworthy for quality delivery of education in school.