Self-regulated learning is the process of developing a child's self-regulation skills that affect the overall child development and thus the development of preschoolers’ skills. Self-regulated learning is important for successful coping with the challenges of lifelong learning and especially for the development of a key competence learning to learn. The main aim of the paper was to study the conditions and activities stimulating the self-regulation of the behaviour of preschool children and their correlation with the degree of adoption of the graphomotor, pre-reading, and pre-mathematics skills related to preparation for writing learning. The study was conducted on a sample of 106 children aged 5 to 7 and 30 educators. The study used an environmental assessment scale and self-regulation stimulating activities from the perspective of the educators and a test for the evaluation of the graphomotor, pre-reading, and pre-mathematics skills. The results show that the perceptions of educators on the subscales are greater in assessing the benefits of self-regulation incentives and lower on the assessment of the opportunities and conditions for assisting in the encouragement of self-regulation. Likewise, the results confirm that there is no statistically significant difference in the perception of the educators on the importance of promoting self-regulation regarding their age and years of service. The assignments for the evaluation of the graphomotor, pre-reading, and pre-mathematics skills show the age differences among the children. Older children achieved better results than the younger ones in all the tasks which evaluated the graphomotor, pre-reading, and pre-mathematics skills. It was also found out that the girls were better in graphomotor assignments than boys. The perception of educators to encourage self-regulation among the younger children is mostly negatively correlated with the results of the preschool assessment test, while the correlations with older children are mostly positive. We can conclude that the perception of educators on the importance and ability to provide self-regulation conditions for younger children is mostly not related to or is negatively related to the measured results, while there are statistically significant positive correlations among the older children, suggesting that only older children of preschool age have a satisfactory level of the development of metacognitive skills necessary for self-regulation of learning.