This study investigated pinned-joint bearing strengths and failure behaviors of carbon-fiber-reinforced polyetherketoneketone (CF/PEKK) composites at different temperatures, with varying the width-to-hole diameter (W/D) and edge distance-to-hole diameter (E/D) ratios. Increasing the W/D ratio substantially amplified the pin load capacity, with net tension failure at W/D = 1.5 and bearing failure at W/D ≥ 2, irrespective of temperature. The W/D ratio exerted major influence on the bearing strength, maximum bearing strength was lower at low temperatures (LT; −60 °C) (390 MPa) and high temperatures (HT; 200 °C) (385 MPa) than that at room temperature (RT; 25 °C) (428 MPa). In comparison to RT, a reduction in specimen thickness at bearing area and accelerated localized kink collapse in 0° lamina was observed for LT. The increased ductility of matrix at HT, resulting in fewer matrix cracks. These findings indicate the outstanding bearing load resistance of CF/PEKK composites, supporting their suitability for utilization in high-performance structures.