Decades of psychotherapy research suggest that patient–therapist match accounts for outcome beyond single patient or therapist variables. This study examines the associations between different patterns of patient–therapist matching (in terms of orientation on relatedness or self-definition) and outcomes at termination of psychoanalytic psychotherapy with young adults. Thirty-three patients and their therapists were classified as predominately anaclitic or introjective at baseline. Patients in the convergent patient–therapist dyads (both anaclitic or both introjective) showed significantly greater symptom reduction and increased developmental levels of representations of mother than patients in the complementary dyads (opposite personality configurations). Moreover, convergent patient–therapist match was connected with larger effect sizes on all outcome measures and lower proportion of non-improved patients. These findings suggest the importance of the therapists’ early adjusting their orientation on relatedness or self-definition to their patients’ predominant personality configuration in order to enhance treatment outcomes.