Empirical evidence suggests that Malaysian students encounter challenges when tackling Higher Order Thinking Skills (HOTS) questions. The TIMSS and PISA results highlight the unsatisfactory performance of Malaysian students, indicating a significant achievement gap. Consequently, this study aims to assess the effectiveness of a contextual mathematics learning strategy that integrates the GeoGebra software (referred to as PMK-Geo). Focused on the measurement and geometry subject for form one students, the strategy aims to enhance students’ HOTS, including applying, analysing, evaluating, and creating. A quasi-experimental study was conducted, employing a pretest-posttest non-equivalent control group design. 102 form one students from the same population were divided into three equal groups: two experimental groups (utilising the PMK-Geo strategy and a conventional PMK strategy) and a control group (employing traditional learning methods). The study spanned nine weeks during which quantitative data was collected and analysed. Posttest data for HOTS achievement were collected and analysed. Post-test one-way ANOVA results revealed a significant disparity in post-test score achievements among the three learning strategies [F (2,99) = 60.454, p < .05], with a notable Eta-square effect size (η2 = 0.55). Multivariate Pillai’s Trace test and Univariate post-test analysis indicated a substantial main effect associated with the independent variable of mathematics learning strategy across all four dependent variables: applying, analysing, evaluating, and creating. A comparative analysis of mean scores from pre- and post-tests across the three groups for each cognitive domain revealed that students utilising the PMK-Geo strategy exhibited the most substantial improvements, with the highest mean score differences between pre- and post-tests for all HOTS cognitive domains (mean difference: applying = 3.41, analysing = 4.45, evaluating = 4.70, creating = 3.82). In conclusion, the study’s findings underscore the suitability and efficacy of the PMK-Geo strategy in enhancing students’ HOTS. The study’s implication lies in the potential of the PMK-Geo strategy to enhance form one students HOTS when addressing mathematical challenges within the measurement and geometry domain.

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