This paper presents the results of an investigation into web crippling behaviour—conducted on cold-formed thin-walled steel lipped channel beams subjected to Interior-One-Flange (IOF), Interior-Two-Flange (ITF), End-One-Flange (EOF) and End-Two-Flange (ETF) loading conditions as defined by the American Iron and Steel Institute (AISI). An experimental program was designed to obtain the load-deformation characteristics of beam members with varying cross-sectional and loading parameters under the three web crippling loading conditions. The results obtained from the experiments comprised of the ultimate web crippling strength values and displacements of the thirty-six beam specimens tested. Nonlinear finite element models were developed to simulate web crippling failure of the two loading conditions considered in the experimental program. Also, a combination of elastic analysis with a plastic mechanism approach was employed to investigate the load-deformation characteristics of lipped channel members subjected to the IOF loading condition. The comparison of experimental, finite element and plastic mechanism approach results revealed that the nonlinear finite element models were best capable of closely simulating the web crippling failure behaviour observed in the experiments for all ranges of displacement. Web crippling strength predicted from the Eurocode 3, Part 1.3 [1], and the Polish PN-B-0327 [2] design specifications were also compared with the experimental results and the comparisons indicated considerable underestimations for the range of specimens under EOF and ETF loading conditions.