The cerebellum is an important region responsible for adolescent cognitive function and sleep, and their correlation is expected to show different patterns depending on age and gender. We examined the regional cerebellar gray matter volume (GMV), executive function (EF) and insomnia symptoms to identify their correlation and gender differences in adolescents. Data for a total of 55 subjects' (M = 31, F = 24, 14.80 ± 1.39 years old) were analyzed. The correlations between cerebellar regional GMV and Wisconsin card sorting test (WCST) subcategories showed that EF was better with larger GMV both in males and females. Far more overall correlations with cerebellar regions were observed in boys, with corresponding correlation strength being higher, and differences in localization were also observed in contrast to girls. Larger cerebellar GMV corresponded to better EF in adolescents. Insomnia did not influence the correlations between cerebellar regional GMV and EF, but more severe insomnia in boys correlated to smaller GMV in the right flocculonodular lobe. These results might implicate that the adolescent cerebellum is involved differently in EF dependent on gender.