This article details experimental work performed to evaluate the effects of varying feed rate (0.08 and 0.15 mm/rev) and tool coatings (diamond-like carbon and chemical vapour–deposited diamond) on tool wear modes and hole quality when drilling 30-mm-thick Ti-6Al-4V/carbon fibre–reinforced plastic/Al-7050 stacks in a single-shot operation. At a feed rate of 0.08 mm/rev, the diametrical accuracy of holes produced by both the chemical vapour–deposited diamond and diamond-like carbon–coated drills (6.38 mm diameter) was comparable within a tolerance of ±0.04 mm even after 70 holes. However, in terms of cylindricity, holes machined with chemical vapour–deposited diamond were significantly better than those produced using the diamond-like carbon–coated drills by a factor of ~2 (65.7 vs 140.6 µm). A similar trend was also observed for hole out of roundness. Burr height at hole entry locations (Ti layer) ranged from ~0.03 to 0.08 mm for all trials undertaken at the lower feed rate level; however, the diamond-like carbon–coated drills generated exit burrs which were ~4 times larger than their chemical vapour–deposited diamond-coated counterparts. Subsequent wear analysis showed that diamond-like carbon–coated drills operating at 0.08 mm/rev typically exhibited progressive abrasion, workpiece adhesion and chipping leading to fracture of the tool corner, while fracture due to fatigue was prevalent in tests carried out at the high feed rate level. In contrast, poor adhesion of the chemical vapour–deposited diamond coating to the carbide substrate led to premature flaking, severe chipping and fracture of the drill cutting and chisel edge.