Adolescents with sickle cell disease (SCD) need assistance in developing the knowledge and skills that contribute to increased disease self-management and successful transition to adult-based health care. This study evaluated the preliminary psychometric properties of the Self-Management Skills Checklist (SMSC and SMSC-C; Adolescent and Caregiver versions), a measure of perceived SCD-specific knowledge and skills. A retrospective cohort study included 114 adolescents (mean=15.6 y) and their caregivers. We examined internal structure and reliability, score changes over time, and group differences. Cronbach coefficient alphas were 0.79 and 0.74 for caregiver-reported Skills and caregiver-reported knowledge, respectively, and 0.77 and 0.44 for adolescent-reported skills and adolescent-reported knowledge, respectively, indicating good internal consistency for 3 of the subscales. Poor reliability in the adolescent-reported knowledge summary score and factor analysis suggest an interpretation item-by-item, independent of one another. Participant group differences in age and chronic transfusion treatment existed in both summary and subscale scores of the SMSC and SMSC-C. Follow-up administrations of the scales indicated an increase in caregiver-reported skills for their adolescents from time 1 scores (M=3.72±0.83) to time 2 scores (M=3.99±0.63) (t16=2.178, P=0.045). Findings provide preliminary support for the usage of the SMSC and continued development to improve its psychometrics.