We investigated the extent to which clinician-assigned diagnoses of emotional and behavioral disorders and clinicians’ perceptions of client change are consistent with structured measures of youth clinical functioning and parent/family characteristics within the context of usual care or “real world” psychotherapy. A total of 54 therapists from two publicly-funded youth outpatient mental health clinics and 128 youths and parents from the therapists’ combined caseloads were included in the study. Clinician-assigned diagnosis and youth and family demographics were collected at the initial visit, clinician-reported perceived client change was collected at 6-month follow-up, and structured measures of youth clinical functioning and parent/family characteristics were collected at both time points. Results indicate some overlap between clinician-assigned diagnosis, clinician-reported perceived client change, and structured measures of youth clinical functioning and parent/family characteristics after controlling for demographic factors. Results are discussed in terms of implications for the implementation of evidence-based practices in real world community settings.