Bullying continues to be a social issue affecting millions of students of all ages worldwide. Research on bullying seems to be dominated by quantitative research approaches employed standardized categories and measures, ultimately limiting our knowledge about children’s own view on bullying. Our research follows another direction, aiming to explore the representation of bullying in a sample of Italian primary school children by using and comparing the functioning of two qualitative research instruments: interviews, and children’s drawings. In addition, aided by quantitative analyses, we aimed to investigate whether students’ involvement in different bullying roles (as bullies, victims, or defenders), as measured by self-assessment, correlated with different characteristics of the representation of bullying emerging from children’s drawings and interviews. We recruited a convenient sample of 640 primary school students (mean age = 9.44; SD = 0.67), 53.3% of whom were male. The results showed that all forms of bullying, i.e., physical, verbal, and social bullying, could be identified in interview and drawing data, although references to all types of bullying were more frequent in interview data. In terms of bullying criteria, the presence of a power imbalance between the bully and the victim was most frequently detected in both the interview data and the drawing data, while repetition was more easily detected in the interview data. The interview data showed that sadness was the most frequently reported victim emotions, followed by fear, anger, and lack of emotion. The drawing data showed a similar pattern, although victims were more frequently described as lacking emotions compared to the interview data. In both interview and drawing data, age and female gender were positively associated with references to verbal bullying, and negatively associated with references to physical bullying. Additionally, bully/victim children were more likely than uninvolved children to depict physical bullying in the drawings, while this association was not detected in interview data. In summary, our study shows that, compared with drawings, interviews tend to provide a more comprehensive view of children’s own representation of bullying, while drawing data tend to show stronger connections with children’s current personal experiences of bullying.