This paper focused on a newly engineering use flattened-bamboo composite (FBC) and studied the effect of fiber orientation angle (0° - 90°, 15° intervals) on FBC’s embedment performance and failure modes by half hole test. The results indicated that with larger fiber orientation angle, both the embedment strength and initial stiffness gradually decreased (embedment strength: 52 ∼ 26 MPa, initial stiffness: 27062 ∼ 11149 kN/mm), and Hankinson’s formula could effectively predict FBC’s embedment strength with error less than ±7 %. Combing the experimental phenomenon and scanning electron microscope (SEM) results, the failure modes of embedment specimens were classified. For angles of 0° and 15°, the failure mode was a mix of fiber crushing failure and split failure between fibers. For angles from 30° to 60°, the phenomenon of fiber being crushed became less obvious, only small cracks were witnessed around the half-hole area. For angles of 75° and 90°, the bamboo fiber compression failure perpendicular to fiber direction dominated, and two horizonal cracks happened on both sides of the specimen. A damaged constitutive model using continuum damage mechanics was proposed for simulating FBC’s embedding failure modes, and the proposed model was verified by comparing with the experimental phenomenon.