The accurate assessment of psychopathological behaviours of adolescents and young adults is imperative. Symptom Checklist-90-Revised (SCL-90-R) is one of the most comprehensive and widely used scales addressing this purpose internationally. Interestingly, associations between the different SCL-90 symptoms and family functioning have been highlighted. Nevertheless, the scale's factorial structure has often been challenged. To contribute in this area, this study scrutinizes the psychopathological dimensions of the Symptom Checklist-90-Revised (SCL-90-R) in a large cohort of high school students (Mean age = 16.16; SD = .911) from Greece. It addresses this aim by: a) using first order and bi-factor confirmatory factor analysis, and exploratory structural equation models and; b) investigating the factors' associations with family functioning. A total of 2090 public Greek High School students completed the SCL-90-R and the Family Adaptability and Cohesion Scale IV (FACES-IV) covering family functioning, satisfaction and communication. Six different solutions, yielded by separate permutations of CFA, ESEM, and bifactor models, were evaluated. Based on global fit, the clarity, reliabilities and the family functioning links of the dimensions in the models, the ESEM oblique model with the theorized nine factors emerged as the optimum. This model had adequate fit, and symptom dimensions were well defined. Also six of the nine factors demonstrated external associations with family functioning, satisfaction and communication. The clinical assessment benefits of these results are discussed.