This study explores the level of congruency between students’ ratings of their own emotional and behavioral strengths and difficulties, and their teachers’ ratings of these factors, when compared amongst two neighboring countries, Estonia and Finland. Secondly, it investigates the level of agreement between sixth grade students’ ratings and their teachers’ ratings of their emotional and behavioral strengths and difficulties, within each country. Both the students’ version (aimed at 11–17-year-olds) and teachers’ versions of the Estonian and Finnish Strengths and Difficulties Questionnaire (SDQ) were used in the study to measure these issues. No gender differences were found between the students’ overall SDQ scores. However, girls experienced a greater number of emotional problems than boys did. In general, Estonian teachers reported more externalized problems among their students compared to Finnish teachers. Finnish teachers, however, reported more emotional problems among their students. The findings suggest that, in both countries, estimations by teachers and students regarding existing emotional and behavioral difficulties are mismatched. These findings extend the findings of earlier research and provide indications for future teacher training.