The purpose of the study was to examine the effect of challenges that affect the teaching of ordinary level mathematics using dialogue and argumentation approach in the mathematics classrooms in Zimbabwe. A descriptive survey was the method employed for the research. The subjects of this study consisted of approximately 100 Ordinary level Mathematics teachers and ten Mathematics Head of Departments selected from 72 public high schools in Gutu district of Masvingo province in Zimbabwe. Purposive sampling was used for selecting ten participating Mathematics Head of Departments for qualitative data. Random sampling was used for selecting samples of teachers for quantitative research. Quantitative data analysis was done using two statistical metrics namely the mean and the standard deviation while qualitative data was analysed by thematic analysis. The empirical findings of the study indicated that challenges such as class size, planning, attitudes, heterogeneity, lack of confidence, and lack of proficiency among challenges that have a significant but negative influence on the application of dialogue and argumentation in the teaching of Ordinary level mathematics. The main study limitation was that the results may not be transferable nationally since the study was limited to schools in the Gutu district of Masvingo province in Zimbabwe. These results have implications on the need for mathematics teachers to receive training on how to plan and implement the dialogue and argumentation teaching approach in the mathematics classrooms.