High-performance polymer composites are being increasingly favored for structural applications. For this purpose, efforts are being focused on exploring the potential of high-performance thermoplastics and thermosets. Cyanate ester (CE) resin is a special thermoset that can be used at up to 400 °C without any considerable degradation; however, its tribological properties are not at the adequate level. Hence, it is needed to use this polymer in composite form with the fibrous/particulate reinforcement to impart better tribological properties and mechanical strength via a strong fiber–matrix interface. Carbon fiber/fabrics are at the forefront as reinforcement for specialty polymers. The tribological and tensile properties of cyanate ester (CE) composites-filled graphite, polytetrafluoroethylene (PTFE), and MoS2 micron-sized fillers reinforced with carbon fibers (CF) are investigated experimentally in a block-on-ring setup at 100 N, for 10 h, and with a sliding distance of approximately 10,000 m, against a hardened polished 100Cr6 steel shaft and diamond-like-coated (DLC) 100Cr6 steel shaft. The tribological properties of the composites including the coefficient of friction and specific wear rate are enhanced especially with the incorporation of graphite fillers. The friction coefficient and wear rate of the graphite-based composite was decreased significantly at 5 wt.% of graphite concentration. Further, at the same concentration, the graphite-based composite showed superior tensile properties as compared to the reference system owing to better dispersion and adhesion between the fibers and matrix. Tensile tests are performed to characterize the fiber–matrix interfacial adhesion and other strength properties.