This paper presents a novel convolutional neural network (CNN)-based approach for predicting bolt clamping force in the early bolt loosening state of bolted structures. The approach entails tightening eight bolts with different clamping forces and generating frequency responses, which are then used to create a similarity map. This map quantifies the magnitude and shape similarity between the frequency responses and the initial model in a fully fastened state. Krylov subspace-based model order reduction is employed to efficiently handle the large amount of frequency response data. The CNN model incorporates a regression output layer to predict the clamping forces of the bolts. Its performance is evaluated by training the network by using various amounts of training data and convolutional layers. The input data for the model are derived from the magnitude and shape similarity map obtained from the frequency responses. The results demonstrate the diagnostic potential and effectiveness of the proposed approach in detecting early bolt loosening. Accurate bolt clamping force predictions in the early loosening state can thus be achieved by utilizing the frequency response data and CNN model. The findings afford valuable insights into the application of CNNs for assessing the integrity of bolted structures.