Commerce is essentially the exchange of goods and services in various forms between sellers and buyers, together with associated financial transactions. Electronic Commerce (EC) is the process of conducing commerce through electronic means, including any electronic commercial activity supported by IT (information technology) (Adam and Yesha, 1996; Kambil, 1997; Yen, 1998). In this sense, EC is not totally new. Industries have used various EC platforms such as advertising on TV and ordering by telephone or fax. Internet Commerce (IC), or Web Commerce, is a specific type of EC (Maddox, 1998; Minoli D. and Minoli E., 1997). While some traditional EC platforms such as TV and telephone have been used to build “TV-gambling” and “telephone-betting” systems for conducting lottery business, Internet Lottery Commerce (ILC) has been assessed as the most promising type of EC in the foreseeable future. There are many social and moral issues relating to the conduct of lottery business on-line. However, this chapter does not debate these but deals only with business and technology issues. The purpose of this chapter is to provide a structured guide to senior executives and strategic planners who are planning on, or interested in, ILC deployment and operation. The guide consists of several stages: (1) an explanation of the industry segment’s traits, value chain, and current status; (2) an analysis of the competition and business issues in the Internet era and an evaluation of the strategic resources; (3) a planning framework that addresses major infrastructure issues; and (4) recommendations comprising the construction of an ILC model, suggested principles, and an approach to strategic deployment. The chapter demonstrates the case for applying the proposed guideline within the lottery business. Faced with a quickly changing technological context, it pays special attention to constructing a conceptual framework that addresses the key components of an ILC model. ILC fulfils the major activities in a lottery commerce value chain—advertising, selling and delivering products, collecting payments for tickets, and paying prizes. Although the guideline has been devised for lottery businesses, it can be applied to many other industry sectors.