The potential of information technology (IT) to support or augment a competitive business strategy has been recognised for as long as IT has been used in business. There are many examples of information systems (IS.) which are claimed to have created and sustained competitive advantage, allowed beneficial collaboration. or to have simply ensured the continued survival of the organisations which used them. This paper looks at eight of the 'classic' examples of IT applications which are claimed to have been particularly effective in linking the competitive use of technology with business strategy. It then analyses the effectiveness of the use of the technology from the standpoint of one of the commonly-accepted business strategy frameworks. The framework is further used to question the linkage between the business strategies behind the applications and The IT mechanisms which were apparently developed to make these competitive strategies effective.