In order to solve the equilibrium problem related to compaction degree, structural integrity of skid resistance, and skid resistance of asphalt wearing layer on a concrete bridge deck, the influence of rolling mode on compaction degree, structural integrity of skid resistance, and skid resistance performance was analyzed according to compaction curve characteristics, image processing technology, and laser method from the compaction mechanism and temperature control of rolling equipment. The results showed that the compaction degree and rolling times of an SMA-13 asphalt wearing course on the bridge deck could be characterized by a logarithmic model, and the model parameters had clear physical significance. Compared with the vibratory roller, the oscillation roller could achieve a greater and more stable compaction degree of the mixture and maintain a better density, compaction degree, and void ratio after 5 times of oscillation rolling. The pavement wear characteristics were extracted by a digital image method. The results showed that with the increase in rolling times, the rolling temperature decreased gradually, and the wear rate of surface texture increased significantly. The multiscale evaluation of pavement antiskid performance by a laser method showed that the surface structure gradually decreased and tended to be stable (1.2 mm) with the increase in rolling times of the vibratory roller, the microscopic texture density increased with the increase in rolling times, and the proportion of acute angle (<90°) in the peak angle of the surface texture profile decreased with the increase in rolling times. The SMA-13 asphalt wearing course on the bridge deck was rolled by a vibratory roller for 6 times, so as to achieve the balance of compaction degree, structural integrity, and skid resistance.