As a qualifier, he reached the fourth round of the 2009 Sony Ericsson Open, defeating Nicolás Almagro and Tommy Robredo in the process. He lost to Roger Federer in the fourth round, 3–6, 2–6. Despite the scoreline, the first set was a very entertaining encounter, with Federer's longest service game lasting just short of a quarter of an hour; Dent had eight break point opportunities. He had a poor run of form following this, but reversed the poor form by qualifying for Wimbledon, having entered the qualifying via a wildcard. He won his way through to the main draw, where he lost to Daniel Gimeno-Traver in five sets in the first round.