Businesses operate in value chains to pursue a common goal. Information Technology (IT) is used pervasively to support such complex globalised chains, underlined by Business-to-Business (B2B) collaboration activities. Existing B2B collaborations are often inhibited by costs and long setup time. One of the key challenges is to pervasively connect partners across the entire value chain, with the appropriate service offerings.Thus, it is vital to quickly identify potential partners to form new B2B collaboration or to support formed collaborations with swift decision making abilities.This research proposes a contextaware approach to support such B2B collaboration.Context-awareness relates to the use of situational information (e.g. location of user/company, time and date of expected cargo arrival) for decision-making. The decision could be very computing-centric such as a context-aware database query and search for example. In B2B, the action (or decision) could be when to schedule the next delivery or how to identify suitable partners for collaboration. To realise this context aware approach, several issues have been addressed:• Understanding and identifying relevant context in B2B collaborations, thereby formulating an appropriate B2B Context Model,• Identifying a relevant context representation and reasoning technique to process the model, and • Developing a method to support decision making, based on a given context of collaboration.This thesis documents the investigations conducted to establish the viability of this context-aware approach for B2B collaboration. A review of existing context-aware literature revealed that existing context elements defined in other application domains are insufficient for B2B collaboration. Hence, there was a need to further identify B2B ATTENTION: The Singapore Copyright Act applies to the use of this document. Nanyang Technological University Library A Context-aware Approach for Business-to-Business Collaboration iii specific contexts, where inspiration was taken from existing literature on supplier selection criteria. A B2B Context Model to support context-aware B2B collaboration was then formulated based on the reviews. This model is anchored on the three main aspects of context, namely User, Temporal and Location. To ensure that the model is able support different B2B applications, it was verified for completeness with the PIPs (Partner Interface Processes) specifications of RosettaNet, an industry de-facto B2B collaboration standard. Description Logic (DL) was then explored as a theoretical underpinning of the representation and reasoning of context information. This is to ensure decidability and completeness in the reasoning. The B2B Context Model was realised using a DL-safe version of OWL (Web Ontology Language). Experiments conducted using the OWL knowledge base showed that such applications are not scalable. As such, though DL-safe representation ensures sound reasoning, further empirical investigations in this research are based on an XML schema representation, for perf...