Bogdanovic's projected entry into the World's Top 50 did not materialise. In a poor start to 2008, he was involved in Great Britain's Davis Cup defeat by Argentina and slipped out of the Top 200. His poor 2008 continued, with wildcard entries for the Artois Championships and Wimbledon men's singles tournament resulting in defeats. At Wimbledon he faced Simone Bolelli from Italy and lost in four sets 6–7, 6–4, 3–6, 6–7, his seventh consecutive defeat in the first round at Wimbledon. This low was followed by a victory in the Challenger Banque Tournament in Canada, which helped boost Bogdanovic back into the Top 200, for a short period at least.