Under in-plane compressive load conditions, the growth of a delamination initially induced by an impact can be followed by a fast growth after a threshold level, which leads to a catastrophic failure in composite structures. To avoid reaching this critical level, it is essential to uncover the delamination size and growth pattern in real time. Ultrasonic Guided Waves (UGW) have a strong capability to interrogate and monitor the structure in real-time and thus track the growth of damage, which may occur during the flight cycles. Although various types of damage affect the monitored UGW signals, it is challenging to determine from the UGW signals what types of damage and at what rate of growth are occurring within the structure. UGW signals can be acquired at defined intervals and then analysed to possibly detect different types of damages, such as delamination, and to quantify the rate of damage growth over fatigue cycles. However, correlating the UGW-based Damage Indicators (DIs) with the specific type of damage, such as delamination, and damage growth is a challenging task as the relation between these DIs and the actual damage state is very complex. Therefore, in this study, a supervised Deep Neural Network-based (DNN) prediction model is proposed aiming to diagnose the delamination size of the composite structure by correlating the UGW-based DIs with the quantified time-varying delamination size. UGW data is collected through a network of permanently installed piezoelectric transducers (PZTs). The delamination size is obtained through ultrasonic C-Scan technique at defined cycles. DIs are extracted in time, frequency, and time-frequency domains and used as the input for the DNN-based regression model. Each sensor-actuator path is considered as an independent set of indicators, which are separated for training, validation, and testing purposes. The effect of the different paths on the delamination size prediction is presented along with the model performance on measured delamination growth in woven type composite sample.