The relevance of the present issue is caused by a strong need to conduct monitoring processes in all types of teaching processes and a poor development of theoretical, content and technological, scientific and methodological material for teachers' monitoring skills development during their teaching practice. The aim of the article is to create and test a structural and functional model of teachers' monitoring skills development based on a systematical activity-oriented approach. Modelling is the main method in the research as it helps to consider the present problem as a process of a directed and conscious acquisition of monitoring skills by teachers trained. The article presents a fully elaborated structural and functional model of teachers' monitoring skills development which consists of interconnected motivational and aim-oriented, content and procedural, result-oriented and estimation components. The model adapts teachers to new conditions of modern education and encourages for further high quality education monitoring process.