As a promising structural health monitoring (SHM) technology, guided wave (GW) imaging is gaining increasing attention for crack monitoring of aircraft structures. However, actual fatigue crack propagation is a complex dynamically evolving process affected by various variabilities. It is still challenging to accurately track and quantify the dynamic fatigue crack propagation with GW imaging methods. Therefore, in order to achieve more accurate fatigue crack quantification, this paper proposes a multi-scale deep residual network-based GW imaging evaluation method. A convolutional neural network (CNN) is utilized to evaluate the entire pixel distribution of GW imaging maps to fuse damage-related information from multiple GW monitoring paths. By designing multi-scale convolutional kernels and deep residual learning, a robust quantitative image feature extraction is ensured with the dynamic evolution process of fatigue crack growth and the performance degradation is avoided as the CNN goes deeper, thereby improving the quantification accuracy. The method is validated on a fatigue test of landing gear beams, which are important load-carrying aircraft structural components. The results demonstrate that the proposed method can extract multi-scale crack length-related features and accurately track fatigue crack propagations. For batch specimens, the maximum quantification error is reduced from the original 6.1mm to 1.6mm, marking a significant improvement.