The invention discloses an anti-loose bolt set composed of a stop washer and an annular groove nut and an operation method thereof. Through interaction of upright external teeth of the stop washer anda wedge-shaped groove face of the annular groove nut, one radial acting force is added besides axial pretightening force when thread pairs are pretightened, and larger pressure and friction force areformed between the thread pairs. Meanwhile, an additional friction acting point is further added due to the interaction of upright external teeth and the wedge-shaped groove face, thus additional pressure and friction force are increased, the total friction force limit value is increased and is much larger than a friction force limit value generated by a common pretightening bolt, the anti-loosebolt set is better in anti-loose effect, and thus the thread pairs can be prevented from rotating relatively. The anti-loose bolt set is good in reliability and practicability, and can be used for places with severe impact, vibration and alternating load or with large temperature change, maintenance and overhauling of thread connection is reduced effectively, the safety of utilizing of the anti-loose bolt set is improved, and the utilization rate of the anti-loose bolt set is increased.