Delamination represents one of the most significant and dangerous damages in composite plates. Recently, many papers have presented the capability of structural health monitoring (SHM) techniques for the investigation of structural delamination with various shapes and thickness depths. However, few studies have been conducted regarding the utilization of convolutional neural network (CNN) methods for automating the non-destructive testing (NDT) techniques database to identify the delamination size and depth. In this paper, an automated system qualified for distinguishing between pristine and damaged structures and classifying three classes of delamination with various depths is presented. This system includes a proposed CNN model and the Lamb wave technique. In this work, a unidirectional composite plate with three samples of delamination inserted at different depths was prepared for numerical and experimental investigations. In the numerical part, the guided wave propagation and interaction with three samples of delamination were studied to observe how the delamination depth can affect the scattered and trapped waves over the delamination region. This numerical study was validated experimentally using an efficient ultrasonic guided waves technique. This technique involved piezoelectric wafer active sensors (PWASs) and a scanning laser Doppler vibrometer (SLDV). Both numerical and experimental studies demonstrate that the delamination depth has a direct effect on the trapped waves' energy and distribution. Three different datasets were collected from the numerical and experimental studies, involving the numerical wavefield image dataset, experimental wavefield image dataset, and experimental wavenumber spectrum image dataset. These three datasets were used independently with the proposed CNN model to develop a system that can automatically classify four classes (pristine class and three different delamination classes). The results of all three datasets show the capability of the proposed CNN model for predicting the delamination depth with high accuracy. The proposed CNN model results of the three different datasets were validated using the GoogLeNet CNN. The results of both methods show an excellent agreement. The results proved the capability of the wavefield image and wavenumber spectrum datasets to be used as input data to the CNN for the detection of delamination depth.