The purpose of this study was to enhance the detection accuracy for pine-wilt-diseased trees (PWDT) using time series UAV imagery (TSUI) and deep learning semantic segmentation (DLSS) techniques. The detailed methods to accomplish the research objectives were as follows. Considering the atypical and highly varied ecological characteristics of PWDT, DLSS algorithms of U-Net, SegNet, and DeepLab V3+ (ResNet18 and 50) were adopted. A total of 2350 PWDT were vectorized at 9 sites, and 795 images of 2000 damaged trees were used as training data and 200 images where 350 PWDT were found, were used as the test dataset. The felled trees were tracked and the pest-controlled trees were used as to ground truth the TSUI of at least 2 years to ensure the reliability of the constructed learning data. The results demonstrated that among the evaluated algorithms, DeepLab V3+ (ResNet50) achieved the best f1-score (0.742) and also provided the best recall (0.727). SegNet did not detect any shaded PWDT, but DeepLabV3+ (ResNet50) found most of the PWDT, especially those with atypical shapes near the felled trees. All algorithms except DeepLabV3+ (ResNet50) generated false positives for browned broadleaf trees. For the trees, all algorithms did not detect PWDT that had been dead for a long time and had lost most of their leaves or had turned gray. Most of the older PWDT have been logged, but for the few that remain, the relative lack of training data may be contributing to their poor detection. For land cover, the false positives occurred mainly in bare ground, shaded areas, roads, and rooftops. This study thus verified the potential use of semantic segmentation in the detection of forest diseases such as PWD, while the detection accuracy is anticipated to increase with the acquisition of adequate quantities of learning data in future.