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This study takes a closer look at Form Four students’ initial mathematical modelling process when solving mathematical problems using GeoGebra. The modelling process was observed from cognitive perspective to learn the difficulties students faced during the process and the result would give ideas for intervention. Qualitative approach by using multiple case study method was employed. Four participants from Form Four level without prior experience in mathematical modelling were selected. Three different data collection methods were employed and triangulated as well as compared with the idealised modelling cycle to reconstruct individual students’ initial mathematical modelling process. Findings from this study showed the importance of situation model and real model with extra-mathematical knowledge (EMK), students partially follow the idealised modelling cycle, novice modellers do display intuitive ideas in displaying their mathematical process and GeoGebra’s usefulness was learned.