Air-assisted spray technology is widely applied in high-efficiency pesticide applications. The resistance characteristics of the crop canopy reflect its energy dissipation effect on the assisted airflow, connecting the structure of the crop canopy, assisted airflow velocity, and droplet deposition effect. Using a common broad-leaf crop canopy as the research object, the resistance characteristics of the crop canopy in the air-assisted field were investigated in this study by performing theoretical analysis and wind tunnel tests. Further, the feasibility of using the resistance characteristics of the crop canopy was assessed to evaluate its droplet deposition effect. The results showed that under the conditions of different number of leaf layers and initial leaf azimuth angles, the canopy pressure drop experiences a non-linear increasing trend with increasing assisted airflow velocity and that its regression function conforms to the Darcy–Forchheimer function. Moreover, when the initial azimuth angles of single- and multi-layer leaves were 90°–270°, the change rate of the canopy pressure drop with airflow velocity was 7–9 m/s, and there was a critical wind speed. However, with an increasing number of leaf layers in the crop canopy and changes in the initial leaf azimuth angle, the corresponding changes between the maximum canopy pressure drop and resistance coefficient were non-linear. Thus, it is proposed that the resistance characteristics of multi-layer leaves cannot be quantified as the results of the linear superposition of the resistance characteristics of several single-layer leaves—that is, it should be regarded as a whole research object. Combined with the analysis of the influence of the crop canopy resistance on droplet deposition, it is considered that when the crop canopy has multiple leaf layers in the airflow direction, the existing air-assisted spray technology cannot guarantee droplet deposition and canopy penetration simultaneously.