Use of strategic questioning as the formative assessment is one of the strategies that advocates the improvement of learners' performance in Mathematics. The study assessed the contribution of strategic questioning to the improvement and development of the foundation of knowledge of learners to come up with improved performance and developed a plan of strategic questioning. The experimental evaluation design-posttest only was used with posttest for both control and experimental groups. The experimental groups were exposed to the treatment. Data gathered through a checklist and plan for strategic questioning were developed. Two hundred twenty-five students under the researcher were randomly selected as control and experimental groups. Data were statistically treated with percentage, mean, standard deviation, t-test, and p-test. It was found out that there was a significant difference between the performance of students in the controlled and experimental groups after instruction/intervention. This meant that strategic questioning as formative assessment contributes to the effective performance of the learners in mathematics. It can be inferred further that categorizing questioning to the lower level and higher level can really increase the learners' performance in math. The research revealed then that using contextualized problems/lessons as one form of strategic questioning in every quarter contributed to improving the learners' competence in solving math problems.