A Ground Penetrating Radar (GPR) system based on a ground-coupled, densely populated antenna array was used to collect data during an infiltration experiment conducted at a test site near the Tottori Sand Dune, Japan. The antenna array used in this study consists of 10 transmitting antennas (Tx) and 11 receiving antennas (Rx). For this experiment, the system was configured to use all possible Tx-Rx pairings, resulting in a Multi-Offset Gather (MOG) consisting of 110 Tx-Rx combinations. The array was left stationary at a position directly above the infiltration area and data were collected every 1.5 seconds using a time-based trigger. Common-Offset Gather (COG) and Common Mid-Point (CMP) data cubes were reconstructed from the MOG data during post-processing. There have been few studies that used time-lapse CMP data to estimate changes in velocity of propagation. In this study, electromagnetic (EM) wave velocity was estimated heuristically at 1-minute intervals from the reconstructed CMP data through curve fitting, using the hyperbola equation. We then proceeded to calculate the depth of the wetting front. The evolution of the wetting front over time obtain through this method is consistent with the observations from a soil moisture sensor which was placed at a depth below 20 cm. The results obtained in this study demonstrate the ability of such array GPR system to monitor a subsurface dynamic process like water infiltration accurately and quantitatively.