Toe muscular strength plays an important role in enhancing athletic performance because the forefoot is the only part of the body touching the ground. In general, muscular strength increases with age throughout adolescence, and sex-related difference in muscular strength becomes evident during childhood and adolescence. However, toe muscular strength is known to be levelled off after late adolescence in both sexes. For adolescent populations, therefore, the association of toe muscular strength with physical performance might differ with age and/or sex. This study aimed to investigate differences in relationships between toe muscular strength and vertical jump performance across sex and age in adolescent populations. The maximum isometric strength of the toe muscles and vertical jump height (VJ) were assessed in 479 junior high school students (JH) aged 12-14 years (243 boys and 236 girls) and 465 high school students (HS) aged 15-18 years (265 boys and 200 girls). Two types of measurements were performed to evaluate the toe muscular strength: toe gripping strength (TGS) with the metatarsophalangeal joint in the plantar flexed position and toe push strength (TPS) with the metatarsophalangeal joint in the dorsiflexed position. TGS and TPS were normalized to body weight. Two-way ANOVA showed that TGS had significant main effects of sex (boys > girls) and age (HS > JH) while TPS only had a significant main effect of sex (boys > girls). When the effects of sex and age were separately analyzed, VJ was significantly correlated with TGS in JH girls, HS girls, and JH boys (r = 0.253-0.269, p < 0.05), but not in HS boys (r = 0.062, p = 0.3351). These results suggest that toe muscular strength is relatively weakly associated with vertical jump performance in adolescent boys and girls, but the association would not be established in high school boys.