Prior work has indicated that female adolescents mature more quickly than males with regard to the various personality dimensions. From the developmental perspectives, this study aimed to explore gender differences in the relationships between resilience and the Big Five personality traits in Japanese adolescents. Middle school students (N = 310, 155 females, age range = 14–15 years) participated in an online survey. The results demonstrated that females had higher Conscientiousness than males. Stepwise regression analyses indicated that Neuroticism was the most influential predictor of resilience in females, whereas Extraversion was the most important predictor in males. Multigroup path analysis demonstrated that the effect of Neuroticism on resilience was greater for females; however, the effects of all other variables did not differ across genders. Considering gender differences is important to understand the relationship between resilience and the Big Five dimensions among adolescents.