The study analyzed the effectiveness of Contextualized Differentiated Instruction (CDI) in the teaching of Contemporary Issues, a Social Studies subject in Grade 10 with these of objectives by: (1) Determining its pre-post-test results; (2) Testing its significant mean difference; (3) Analyzing its learning competencies and identifying appropriate strategies; and (4) Formulating an enhanced CDI Model of Contextualized Teaching and Learning (CTL). A one group quasi-experimental design, using pretest-and-posttest, determined the respondents’ performance on Contemporary Issues. A significant difference in the pre-posttest demonstrated an increase of proficiency manifested by an increase in the mean scores and enhanced qualitative equivalents. An above proficiency level revealed in the posttest was attributed by the engagement of the respondents in the learning process using contextual differentiated learning activities. Matching the learning competencies with the three learning domains of Gardner’s multiple intelligences resulted in a substantial utilization of the interactive and prospective teaching strategies, except on the analytic teaching strategies that were found inadequate. Hence, the creation of the COVID-19 Model may juxtapose the essence of an enhanced CDI Model of CTL. The findings have social and practical value to support differentiation of instruction in the 21st century education.