The rapid development of Web technologies and with it the increased demand for quick Web application development has taken the Web development process into a new state. Several academic papers and surveys describe the current state of the Web market as similar to the `software crisis' of the early 60s, when software development practices were ad hoc and unstructured. Developers are realising the need for control, management, and sound modelling languages to document Web applications. This research investigates and empirically evaluates ten of the main Web modelling languages available to the market. A set of eight criteria is identified from the literature. These criteria are then fine tuned and verified in a questionnaire survey targeting fourth generation e-commerce companies in the UK. Respondents of the survey suggest a ninth criterion, which is further verified and added to the list. The author implements these Web models using a real case study, the IPCIS Web application. An empirical evaluation process takes place whereby the outcomes of the Web implementation are evaluated against the verified criteria. The evaluation process helps to verify the research hypothesis and establishes that none of these models meets the market requirements. The recommendations of the evaluation process provide insights into what is missing in these Web models. The survey outcomes are tested for sampling error and statistically projected onto the population as a whole. From these projections, this research establishes that the majority in the market have heard of at least one of the Web models; however, the majority do not use them. Finally this research concludes that the market does believe in the need for Web models yet are disappointed with the current models on offer.