The acoustic emission (AE) technique has become a well-established method of monitoring structural health over recent years. The sensing and analysis of elastic AE waves, which have involved piezoelectric wafer active sensors (PWAS) and time domain and frequency domain analysis, has proven to be effective in yielding fatigue crack-related information. However, not much research has been performed regarding (i) the correlation between the fatigue crack length and AE signal signatures and (ii) artificial intelligence (AI) methodologies to automate the AE waveform analysis. In this paper, this crack length correlation is investigated along with the development of a novel AE signal analysis technique via AI. A finite element model (FEM) study was first performed to understand the effects of fatigue crack length on the resulting AE waveforms and a fatigue experiment was performed to capture experimental AE waveforms. Finally, this database of experimental AE waveforms was used with a convolutional neural network to build a system capable of performing automated classification and prediction of the length of a fatigue crack that excited respective AE signals. AE signals captured during a fatigue crack growth experiment were found to match closely with the FEM simulations. This novel AI system proved to be effective at predicting the crack length of an AE signal at an accuracy of 98.4%. This novel AI-enabled AE signal analysis technique will provide a crucial step forward in the development of a comprehensive structural health monitoring (SHM) system.