Philippines has participated in the Programme for International Student Assessment (PISA) since 2018. The recent results of PISA urged the researchers to think about the possible interventions that the schools can offer to learners. Limited information on the capability of Grade 8 learners to answer PISA questions has prompted the researchers to delve on the study which aims to determine the level of the difficulty of these learners to solve mathematics PISA-like questions focusing on the following topics, namely: sets with the use of Venn diagrams, algebraic expressions, and equations and inequalities in one variable. The self-made questions were validated by five experts, achieving a content validity index of 1.00, and then were subjected for reliability test to 30 participants, resulting in an acceptable Cronbach’s alpha coefficient of 0.739. Out of 3,061 Grade 8 learners, 250 of them were randomly chosen from all public schools, and were interviewed to assess at which stage they were unable to proceed with the solution to the problems. It was found that five to eight out of ten learners were unable to proceed due to a lack of comprehension of the given problem. However, it was noted that only 10% to 30% of learners were able to provide complete and accurate solutions to the problem. To address this, intervention programs were suggested.