Background. Youths with type 1 diabetes transitioning from pediatric to adult care are known to experience significant glycemic excursions and medical complications. Diabetes distress and transition readiness are two potentially related constructs involved in this transition process, but the relationship between them has not been extensively studied. Hypothesis. Lower diabetes distress is associated with increased transition readiness among youths with type 1 diabetes transitioning to adult care. Subjects. One hundred one adolescents and emerging adults with type 1 diabetes transitioning to adult care complete data in 63 study participants. Methods. In this cross-sectional study, we collected diabetes distress scale scores (via T1-DDS) and transition readiness scores (via Am I ON TRAC) at the last pediatric diabetes visit. We fitted regression models to estimate the relationship between T1-DDS scores and ON TRAC scores. Results. The total mean T1-DDS score was associated with ON TRAC knowledge score (β = −2.73, 95% CI −4.41,−1.06, p = 0.002 ), behavior score (β = −2.61, 95% CI −4.39,−0.84, p = 0.005 ), and transition readiness indicator (β = −0.18, −0.34,−0.01, p = 0.03 ). Multiple T1-DDS subscales were associated with ON TRAC knowledge score: powerlessness, management distress, negative social perceptions, eating distress, physician distress, and family/friend distress. Multiple T1-DDS subscales were also associated with ON TRAC behavior score: management distress, negative social perceptions, eating distress, and family/friend distress. Conclusions. Diabetes distress and transition readiness have an inversely proportional relationship in youths with type 1 diabetes transitioning to adult care. Targeting diabetes distress may also improve transition readiness (and vice versa) in this population.