A number of incidents of pile tip damage and extrusion buckling have been reported within the offshore industry, generally arising during driving of relatively thin-walled tubular pile foundations through hard layers or potentially heterogeneous sediments. The issue has become of particular concern with modern trends toward larger diameter piles, with higher ratios of diameter to wall thickness, for monopile or jacket foundations of offshore wind turbines. The paucity of good-quality data available in the public domain about this kind of failure has impaired the development of simple design guidelines for industry to address the issue. The paper presents results from a series of centrifuge model tests where pile tip damage and extrusion buckling were observed during driving of either (1) undamaged cylindrical piles into a sand bed containing a layer of different sizes of boulders, or (2) predented piles into medium dense homogeneous sand. Following a previously reported pilot study, a new and higher energy model pile-driving hammer was designed to permit driving through the hard layers and allow pile embedment by up to five diameters. Two test beds were prepared, one of which contained boulder layers of different sizes either near the surface or at a depth of about one pile diameter, into which piles of two different diameter to wall thickness ratios were driven. The test series led to observations of pile tip damage that ranged from abrupt tip crumpling to gradual extrusion buckling. For 2 of the 22 piles installed, dent growth during installation was detected by optical fiber sensors attached to the piles. For the uninstrumented piles, damage was deduced from the trends in blow counts during installation, with later confirmation from detailed visual inspections and laser scanning, and also from careful layer by layer excavation of each sample. The high-quality database generated from the model tests forms a valuable resource for further study and validation of advanced numerical models to simulate pile tip damage and for calibration of simple guidelines for practical design.