The volatile survival of Internet web sites from the market competition makes us hard to constantly characterize the resulting complicated business ecosystem. The collaboration and competition among Internet business players create a business ecosystem with complex relationships, which need an unobvious way to monitor and understand their development. This thesis proposes an automated monitoring system to monitor the complicated and evolutionary business ecosystem of Internet web sites by observing web site traffic, news and blog articles. In quantitative way, the system automatically detects the potential emerging web sites and determines whether theses web sites flourish continually. In qualitative way, the system extracts multiple relations such as collaborate and compete among business ecosystem of Internet web sites from news articles. The applications of the proposed system helps companies identify emerging web sites when they tend to monitor potential competitors or look for collaborators in real time. Besides, multiple relations of the business ecosystem can help experts identify important roles playing in the Internet web business ecosystem. To reduce the monitoring cost of companies, the system can filter unrelated information on Internet and effectively catch the information related to the evolution of business ecosystem for Internet web sites in real time.