(1) Background: The purpose of this study was to investigate whether the loosening of total knee arthroplasty (TKA) implants could be detected accurately on plain radiographs using a deep convolution neural network (CNN). (2) Methods: We analyzed data for 100 patients who underwent revision TKA due to prosthetic loosening at a single institution from 2012 to 2020. We extracted 100 patients who underwent primary TKA without loosening through a propensity score, matching for age, gender, body mass index, operation side, and American Society of Anesthesiologists class. Transfer learning was used to prepare a detection model using a pre-trained Visual Geometry Group (VGG) 19. For transfer learning, two methods were used. First, the fully connected layer was removed, and a new fully connected layer was added to construct a new model. The convolutional layer was frozen without training, and only the fully connected layer was trained (transfer learning model 1). Second, a new model was constructed by adding a fully connected layer and varying the range of freezing for the convolutional layer (transfer learning model 2). (3) Results: The transfer learning model 1 gradually increased in accuracy and ultimately reached 87.5%. After processing through the confusion matrix, the sensitivity was 90% and the specificity was 100%. Transfer learning model 2, which was trained on the convolutional layer, gradually increased in accuracy and ultimately reached 97.5%, which represented a better improvement than for model 1. Processing through the confusion matrix affirmed that the sensitivity was 100% and the specificity was 97.5%. (4) Conclusions: The CNN algorithm, through transfer learning, shows high accuracy for detecting the loosening of TKA implants on plain radiographs.