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Obtaining a robust fiber/matrix interface is crucial for enhancing the mechanical performance of fiber-reinforced composites. This study addresses the issue by presenting a novel physical–chemical modification method to improve the interfacial property of an ultra-high molecular weight polyethylene (UHMWPE) fiber and epoxy resin. The UHMWPE fiber was successfully grafted with polypyrrole (PPy) for the first time after a plasma treatment in an atmosphere of mixed oxygen and nitrogen. The results demonstrated that the maximum value of the interfacial shear strength (IFSS) of the UHMWPE fiber/epoxy reached 15.75 MPa, which was significantly enhanced by 357% compared to the pristine UHMWPE fiber. Meanwhile, the tensile strength of the UHMWPE fiber was only slightly reduced by 7.3%, which was furtherly verified by the Weibull distribution analysis. The surface morphology and structure of the PPy in-situ grown UHMWPE fibers were studied using SEM, FTIR, and contact angle measurement. The results showed that the enhancement of the interfacial performance was attributed to the increased fiber surface roughness and in-situ grown groups, which improved the surface wettability between the UHMWPE fibers and epoxy resins.