The goal of this research study is to classify damages in an aluminum panel using ultrasonic-guided waves (UGWs). The study is carried out on the premise that only a limited dataset, consisting of only two receivers, is available. In the experimental phase, three distinct parts, that is, stainless steel masses, were located on the surface of the panel, assumed to be mapped into four triangular regions, to experimentally simulate the effects induced by circular artificial damage of varied sizes. UGW-driven damage classification was thus performed via machine learning. A data synthesis technique called conditional generative adversarial network (cGAN) was used to generate 2000 samples (signals) for each of the 12 different malfunction scenarios (classes), based on the combination of damage region and size. Damage features were extracted using the wavelet time scattering technique, while the classification task was performed via a long short-term memory network with tuned hyperparameters. A validation procedure was executed to ensure that the classification network was not overfitted. Furthermore, two testing stages were performed to evaluate the designed framework. The designed framework was thus tested on the observations excluded from the training and validation phases, as well as on 10 additional novel experimental samples. The high accuracy and F1-score values of the validation and the two testing stages—97.7%, 98.5%, and 96.6%, respectively—attest to the generality of this methodology, which is neither underfitted nor overfitted. To further assess the robustness of the methodology, the cGAN was tested on a new sensor placement, demonstrating a consistent performance (95.3%) and confirming the framework applicability under different sensor configurations, showcasing potential extension to other classification problems featuring a limited dataset.