The oil palm trees in Southeast Asia face a great challenge due to voids within tree trunks. Besides, both plantations and the palm oil industry suffered considerable losses due to ineffective inspection of defective trees. Several techniques such as ultrasound, X-ray, capacitive volume, gamma computed tomography, and microwave tomography were applied to detect and control the decay of a trunk. However, all the techniques showed substantial drawbacks (such as limited resolution, tedious processing time, and use of bulky equipment with limited mobility) except for microwave tomography which overtook the other techniques by using a method that distinguishes the dielectric properties of healthy and diseased trunks. This work proposes ultra-wide-band (UWB) signal transmission and reception using antenna sensor arrays that record reflections from affected regions in the trunk. Various factors have been considered, such as different cylindrical arrays of 4, 8, 12, and 16 antennas; different positions of hollows; a heterogeneous trunk; multiple targets; and larger trunk samples (16–30 cm). To validate the system’s capabilities, two cylindrical wood samples with different diameters of 100 mm and 140 mm and with one hollow and three hollows within are 3D-printed, investigated, and then measured. The authors recommended a robust time-reversal algorithm (RTR) to reconstruct 2D images that successfully identified and localized cavities with the smallest diameter of 3.5 mm. Furthermore, reconstructed images of measured data verified a practical and reliable oil palm trunk imaging and sensing system with a high structural similarity index and resolution.