From 1999 to 2008, post-handover Hong Kong, through the joint enterprise of the Special Administrative Region (SAR) Government and the Sports Federation and Olympic Committee of Hong Kong, China, activated international sporting bids thrice, respectively, for the hosting rights of the 2006 Asian Games, the 2009 East Asian Games and the 2011 International Olympic Committee Session. It won the second project, but lost the others. This paper investigates the reason why the city became a keen sporting-event bidder after its retrocession to China, and seeks to understand the causes of the success and the failures. It will also review Chinese authorities’ role in the bids, and comprehend the factors that determined their supporting attitude. In short, all the findings will provide an in-depth account of Hong Kong’s imperfections in handling international sporting affairs and China’s political considerations in interacting with the SAR, even in sporting matters.