To evaluate the skid resistance performance of asphalt pavement under cumulative wheel load and overload, an orthogonal test considering factors such as total traffic volume, occurrence interval, and duration of overload traffic was designed, and lab tests were conducted. This testing was performed based on the self-invented Tire-pavement Dynamic Friction Analyzer (TDFA), by which the real-time data of tire-pavement friction coefficient and pavement textures can be acquired. The results indicated that in the overall process of pavement with different gradation types, all pavement friction coefficients (COF) showed a similar trend of increasing first and then decreasing, and finally tended to be stable. In contrast, the Mean Profile Depth (MPD) values always fluctuated significantly. Moreover, it was found that there is a poor correlation between COF value and MPD value while investigating the degradation laws concerning the skid-resistance performance of asphalt pavement. Compared with the overload traffic applied in the middle and late stage of wear, the deterioration rate of pavement dynamic friction coefficient is faster and the final value of friction coefficient is lower when heavy traffic is applied in the early stage. Finally, the significance of the designed orthogonal test was analyzed. The results show that the total traffic volume has a significant impact on the COF value in the process of pavement service life, followed by the occurrence interval of heavy traffic, and finally the duration of heavy traffic.