This research paper discuses more about the management strategies essentially in Amazon.com and Borders Books businesses. To arrive at the conclusion of this paper statistical analysis related to the topic of discussion was collected and previous works used. Amazon.com is considered the pioneer in online selling. It expanded in the late 1990s to sell the world’s largest selection of books, DVDs, videos, CDs, electronics, toys, tools, house wares, and kitchen gadgets. Through intermediaries’ conformities, Amazon.com in addition sells products from renowned retailers like Toysrus.com Incorporated., the Borders Group, etc. On the other hand, Borders Group incorporated is the largest after Amazon.com in the United States bookstore chains. It is the fastest rising bookstore chain. It runs 354 superstores in the name of Borders Books and Music. It features books and special events, like live music, and appearances by artists. This research paper analyzed and compared two bussinesses on such topics as management approach each took to Internet marketing and sales, three reasons for Amazon’s success despite not turning a profit for the first five to six years, three reasons Borders, although initially successful and profitable, ended up in chapter 11 in relation for bankruptcy safeguard. In conclusion, in order for a company to flourish in the competitive market environment it should adopt the modern marketing strategies like marketing online, designing there website in a way that attracts many customers.