Tottenham Hotspur (“Spurs”) Football Club were once the most entrepreneurial of English football teams, including being the first to obtain a stock market flotation and to attempt to diversify into other areas beyond their core. However, like many football clubs, they were slow to embrace the Internet including more recently the use of social media for marketing. This chapter investigates the history of Spurs’ embrace of the Internet and social media and asks why a club traditionally renowned for its flair and enterprise on the pitch has been so slow to embrace modernity in the digital world.