This study investigates whether the longitudinal association between fearlessness and conduct problems (CP) is mediated by warm and harsh parenting, parent-child conflict, anxiety, and callous-unemotional (CU) traits. The constructs under investigation were assessed at five different time points, spanning a period of eight years. A multi-informant approach was followed, collecting data from parents and teachers (N = 2,121; 47% girls). The structural equation model pointed to both direct and indirect pathways between fearlessness and CP. Specifically, findings suggested that Time 1 fearlessness (age 3-5 years) increased the likelihood of Time 2 (age 4-6 years) harsh parenting and Time 3 (age 5-7 years) parent-child conflict. Further, fearlessness was positively associated with Time 4 (age 8-10) callous-unemotional traits and Time 5 (age 11-13) CP. The total indirect effect from fearlessness to CP through these variables was significant, although the specific indirect effect from fearlessness to CU traits to CP accounted for most of the variance. Warm parenting and anxiety did not mediate the association between fearlessness and CP. In addition to the identified pathways connecting fearlessness to CP, findings pointed to the existence of multiple developmental pathways to future CP, as well as gender differences in longitudinal associations.