Introduction: Restoration of endodontically treated teeth could be challenging for dentists, as these teeth would be biomechanically compromised at multiple levels, such as tissue components and tooth structures.Objectives: This study aimed to evaluate fracture resistance and failure modes of teeth restored with custommilled posts and cores fabricated from polyetherketoneketone, fiber-reinforced resin materials, and prefabricated fiber posts. Material and methods: Thirty mandibular premolars were used in the present study. After endodontic treatment, teeth were randomly assigned into three groups, i.e., MPP: restored with custom-milled posts and cores fabricated from polyetherketoneketone (PEKK); MFP: restored with custom-milled posts and cores fabricated from fiber-reinforced resin; and PFP: restored with prefabricated fiber-reinforced resin posts, then all samples were restored with metal crowns. Samples were subjected to a 45 o shear force at the inner slope of buccal cusp to failure. One-way ANOVA for independent groups and χ 2 test at 0.05 statistical significance were applied. Results: Differences between fracture resistance means of the three groups were not statistically significant (p = 0.279 > 0.05). The fracture resistance means for the MPP group was 423.2 ± 113.28 N; 356.90 ± 141.050 N for the MFP group; and 439.5 ± 100.616 N for the PFP group. As for failure types, no significant difference among the three groups was detected (p = 0.366 > 0.05). Regarding the failure modes, the reparable failure modes in each group, i.e., MPP, MFP, and PFP were 60%, 80%, and 50%, respectively. Conclusions: Teeth restored with custom-milled posts and cores fabricated from PEKK and fiber-reinforced composite displayed an acceptable performance. Consequently, within the limitations of this study, these posts may be considered a good alternative to prefabricated fiber-reinforced posts.