When dental students begin patient care in the clinical curriculum, they are required to move from the well-defined problems of the classroom to the more ambiguous and real life problems encountered in the context of patient care in the clinical setting. This change in learning environment requires development of reflective thinking. Reflective thinking refers to the process of thinking about uncertainty or ill-defined problems. King and Kitchener refer to the outcome of the reflective thinking process as reflective judgement. The purpose of this study was to explore the development of reflective judgement in the initial phase of the clinical curriculum. This exploratory study used a case study approach with qualitative methods. A convenience sample of third year predoctoral dental students (n = 16) volunteered to participate in writing a clinic journal and semi-structured interviews at three time points over a time period of one year. Student compliance in writing clinical journals was poor; therefore the qualitative data was primarily gathered from interview transcripts. The qualitative interview data were analysed using a coding scheme based on King and Kitchener’s Reflective Judgement Model of Intellectual Development. The Cronbach alpha was 0.76 for reliability of the coding scheme. Based on the analysis of interview data, the there was an average growth in reflective judgement over the year from Stage 4.89 to 5.59 for an overall change of +0.70. Additional research is needed to explore the growth in reflective judgement over the final year of the clinical curriculum as well as to identify the most effective educational strategies to facilitate growth in reflective judgment.