Ultrasonic-assisted drilling (UAD) is a machining process that is known to improve the hole quality and reduce cutting forces. Previous studies focused on optimizing cutting parameters to improve the hole quality in conventional drilling (CD) and UAD, as well as to finding the optimum vibration parameters (frequency and amplitude) that will increase the effectiveness of the UAD process. However, the influence of cutting tool type during UAD has been largely overlooked. This research aims to address this gap by analyzing the effect of cutting tool type during UAD on the cutting forces and hole quality in GLARE (Glass Laminate Aluminum-Reinforced Epoxy) laminates. Four types of drills, namely, twist drill (TD), double cone drill (DCD), a step drill type 1 (SD1), and step drill type 2 (SD2) with different step length, were selected for this study. The lowest thrust force (47.04 N) and torque (0.079 Nm) were achieved using twist drill, while DCD, SD1, and SD2 exhibited higher thrust forces (12.81%, 20.69%, 41.3%) and torques (94%, 92%, 91%), respectively. In addition, TD produced high-quality holes with lowest surface roughness (Ra 1.66 μm, Rz 10.58 μm) and minimal burr formation (entry burr height 152.3 μm, exit burr height 69.22 μm). Conversely, DCD, SD1, and SD2 showed higher surface roughness Ra (23%, 16%, 24%) and Rz (16%, 37%, 29%), respectively, compared to the TD. Holes drilled using SD1 and SD2 generally had smaller burr height. Overall, UAD system effectively reduced cutting forces at low spindle speed and feed rate. To achieve higher drilling quality, specifically to reduce the surface roughness and exit burr height, a medium spindle speed of 3000 rpm, a feed rate of 225 mm/min is recommended. Drilling at higher cutting parameters using UAD resulted in a decline in hole quality, except for entry burr height.